Development Of Catalytic Metal Mediated C H Hydroxylation Methods With Improved Functional Group Compatibility

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Development of Catalytic Metal-mediated C--H Hydroxylation Methods with Improved Functional Group Compatibility

Author : James Booker Christianson Mack
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (15 download)

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Book Synopsis Development of Catalytic Metal-mediated C--H Hydroxylation Methods with Improved Functional Group Compatibility by : James Booker Christianson Mack

Download or read book Development of Catalytic Metal-mediated C--H Hydroxylation Methods with Improved Functional Group Compatibility written by James Booker Christianson Mack and published by . This book was released on 2018 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Catalytic C--H hydroxylation methods constitute an enabling technology for the synthesis and structural diversification of organic molecules. Current methods are challenged by substrates that are densely functionalized and contain cross-reactive groups. In recent efforts to address such issues, we have developed two catalytic systems that advance the capability of chemists to functionalize highly complex molecules. Nitrogen-derived functional groups and N-heterocycles are ubiquitous in active pharmaceutical ingredients (APIs) and natural products, but are incompatible with most current chemical methods for oxidation. We describe the development of a new protocol for sp3-C--H hydroxylation. The reaction is performed in aqueous acid with catalytic cis-[Ru(dtbpy)2Cl2] (dtbpy = 4,4'-di-tert-butyl(2,2'-bipyridine)) and enables oxidation of structurally diverse amine- and heterocycle-containing molecules. Tertiary and benzylic C--H hydroxylation is strongly favored over N-oxidation in amine-derived and N-heterocyclic substrates. In efforts to further develop this technology, a multi-pronged mechanistic study was undertaken using techniques such as pressurized sample infusion high-resolution mass spectrometry (PSI-HRMS), 19F NMR spectroscopy, electrochemistry, and reaction kinetics analysis. This work has afforded insight into ligand structure-activity relationships and the identity of relevant active catalytic species. Turnover numbers (TONs) of a series of catalysts examined are strongly correlated to the rate and extent of ligand dissociation that occurs under the reaction conditions. Insights gained from these studies should give way to the design of next-generation catalysts for efficient C--H oxidation of complex molecules. In related studies, we describe the development of a Mn-catalyzed hydroxylation reaction that uses H2O2 or peracetic acid as the bulk oxidant. This method complements our Ru-based chemistry by enabling the functionalization of stronger, less reactive C--H bonds. The protocol features exceptionally low catalyst loadings, accommodates a variety of simple ligands (including 2,2'-bipyridine), and favors 2o alcohol products over the corresponding ketone derivatives. Preliminary studies aimed at understanding catalyst degradation/arrest mechanisms are also described.

The Development of a Metal-free Catalytic Method for the Selective Hydroxylation of Aliphatic C-H Bonds

Author : Nichole Danielle Litvinas
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (613 download)

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Book Synopsis The Development of a Metal-free Catalytic Method for the Selective Hydroxylation of Aliphatic C-H Bonds by : Nichole Danielle Litvinas

Download or read book The Development of a Metal-free Catalytic Method for the Selective Hydroxylation of Aliphatic C-H Bonds written by Nichole Danielle Litvinas and published by . This book was released on 2010 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The diversity and structural intricacies of molecules needed for pharmaceutical, biological, and materials applications have challenged chemists to develop transformative chemical processes that greatly facilitate small molecule synthesis. C-H Bond functionalization represents one such class of reaction types, and is a general problem for reaction discovery that has witnessed an explosion of interest within the past 10 years. Inspired largely by Nature's ability to conduct site- and stereoselective C-H bond oxidation reactions, we have been driven to design small molecule catalysts that can emulate such processes. Our focus has taken aim at the problem of C-H bond hydroxylation, efforts that have yielded a novel, non-metal-based catalytic system for the selective oxidation of tertiary C-H bonds. These findings contrast the large body of literature detailing C-H hydroxylation reactions through transition-metal mediated catalysis. 1,2,3-Benzoxathiazine-2,2-dioxide-based heterocycles have been shown to function as catalysts for C-H hydroxylation with hydrogenperoxide operating as the terminal oxidant. The evolution of this catalytic process, which capitalizes on the unique reactivity of an oxaziridine intermediate, was made possible using density functional theory to help guide reagent design. In addition, kinetic analysis of the stoichiometric oxygen-atom transfer reaction has provided insight into the principal features that influence oxaziridine reactivity. This information coupled with the discovery that reactions could be conducted under aqueous reaction conditions with hydrogenperoxide has resulted in a markedly improved process for tertiary C-H hydroxylation. The reaction occurs stereospecifically and with predictable chemoselectivity in substrates possessing more than one tertiary C-H center. The enhanced performance of this catalytic process has been ascribed to the hydrophobic aggregation of the benzoxathiazinane catalyst and hydrocarbon substrate, which serves to accelerate the kinetically slow hydroxylation event.

Multimetallic Catalytic Methods for the Formation of Carbon-carbon Bonds

Author : Laura Keiko Gilah Ackerman
Publisher :
ISBN 13 :
Total Pages : 186 pages
Book Rating : 4.:/5 (13 download)

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Book Synopsis Multimetallic Catalytic Methods for the Formation of Carbon-carbon Bonds by : Laura Keiko Gilah Ackerman

Download or read book Multimetallic Catalytic Methods for the Formation of Carbon-carbon Bonds written by Laura Keiko Gilah Ackerman and published by . This book was released on 2016 with total page 186 pages. Available in PDF, EPUB and Kindle. Book excerpt: "This thesis describes the use of multiple transition metal catalysts for the selective formation of carbon-carbon bonds. While the majority of cross coupling reactions rely on one transition-metal catalyst which reacts with a stoichiometric metal reagent, the combination of two metal catalysts in reactions has the potential to significantly increase the expediency towards synthetic targets, eliminating the need for stoichiometric metal reagents and improving functional group compatibility. There are many precedents for the combination of catalysts in organic methodology, however relatively few examples of multimetallic catalyzed reactions exist, and even fewer examples exist where the mechanism between the two catalytic metals is understood. The aim of the projects communicated in this thesis is two-fold: (1) To design new and efficient ways to form useful carbon-carbon bonds (Csp2-Csp3, Csp2-Csp2, and Csp2-Csp2) from readily available starting materials and (2) to provide insight into how two transition metal catalysts can cooperate in a reaction to achieve high selectivity and yield. Chapter 1 reviews the importance of carbon-carbon bond formation and introduces the main methods of cross coupling, including the concept of multimetallic catalysis. Previous examples of dual metal catalysis are summarized in the literature and the advantages and challenges of using two metals in a catalytic system are discussed. Chapter 2 presents a nickel and cobalt catalyzed strategy for the formation of Csp2-Csp3 bonds. The first attempted cross electrophile couplings to form diarylmethanes from benzyl halides and aryl iodides is reported in moderate selectivity, followed by the strategic optimization of the co-catalytic system which enables higher yields and selectivity through the coupling of benzyl sulfonate esters with aryl halides. In this reaction, nickel reacts selectively with aryl halides through an oxidative addition step, while cobalt phthalocyanine generates radicals through an Sn2 reaction with benzyl sulfonate esters, followed by homolysis. The extension of this method to coupling benzyl phosphonate esters and primary and secondary benzyl chlorides is also presented. Chapter 3 reports the quest for and ultimate discovery of a multimetallic catalyzed Csp2-Csp2 coupling. Beginning with stoichiometric transmetalation studies for the coupling of aryl C-H bonds with aryl C-X bonds, the reaction of various metal aryl complexes based on iridium, ruthenium, copper, nickel, and palladium are described. While these reactions were ineffective in generating unsymmetrical biaryls, the catalytic combination of a nickel and palladium catalyst to couple aryl bromides with aryl trifluoromethanesulfonate esters for the design of a cross Ullman reaction was a success. This reaction provided access to a variety of unsymmetrical biaryls maintaining an equimolar catalyst loading of the two metals, and showed promise for later development of the formation of useful unsymmetrical bipyridines and dienes. The scope of this remarkable reaction, the origin of selectivity, and the enhancement in rate and selectivity by a KF additive is presented. Additionally, the optimization strategy towards coupling chlorobenzene and electron-rich aryl chlorides is communicated. Finally, this chapter includes the first attempted multimetallic catalyzed multicomponent reactions with the nickel and palladium as well as nickel and cobalt catalyzed systems, including carbonylation, and the difunctionalization of olefins and alkynes."--Pages xii-xiii.

C-H Bond Activation and Catalytic Functionalization I

Author : Pierre H. Dixneuf
Publisher : Springer
ISBN 13 : 3319246305
Total Pages : 269 pages
Book Rating : 4.3/5 (192 download)

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Book Synopsis C-H Bond Activation and Catalytic Functionalization I by : Pierre H. Dixneuf

Download or read book C-H Bond Activation and Catalytic Functionalization I written by Pierre H. Dixneuf and published by Springer. This book was released on 2015-12-18 with total page 269 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.

C-H and C-X Bond Functionalization

Author : Xavi Ribas
Publisher : Royal Society of Chemistry
ISBN 13 : 1849737169
Total Pages : 489 pages
Book Rating : 4.8/5 (497 download)

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Book Synopsis C-H and C-X Bond Functionalization by : Xavi Ribas

Download or read book C-H and C-X Bond Functionalization written by Xavi Ribas and published by Royal Society of Chemistry. This book was released on 2013-05-24 with total page 489 pages. Available in PDF, EPUB and Kindle. Book excerpt: Cross-coupling reactions involving C-H and C-X bond functionalisation are commonplace in natural product synthesis and natural products, therapeutic agents, biological probes, and advanced materials. Much attention has been given to understanding the mechanistic strategies used to achieve this, making this a hot topic in recent years. In this edited book, contributions from across the globe examine these strategies, with a particular focus on palladium and copper, as well as iron – an emerging element in this field. Reviewing the recent literature, the book presents an in-depth understanding of the field, guiding the reader to achieving the best synthetic strategies for aromatic functionalisation. Organic and Organometallic chemists, as well as natural product and pharmaceutical scientists, will find this an essential guide to a major transformation currently underway in synthetic chemistry.

Organic Reaction Mechanisms 2017

Author : A. C. Knipe
Publisher : John Wiley & Sons
ISBN 13 : 1119426197
Total Pages : 672 pages
Book Rating : 4.1/5 (194 download)

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Book Synopsis Organic Reaction Mechanisms 2017 by : A. C. Knipe

Download or read book Organic Reaction Mechanisms 2017 written by A. C. Knipe and published by John Wiley & Sons. This book was released on 2020-07-20 with total page 672 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic Reaction Mechanisms 2017, the 53rd annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2017. The following classes of organic reaction mechanisms are comprehensively reviewed: • Reaction of Aldehydes and Ketones and their Derivatives • Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives • Oxidation and Reduction • Carbenes and Nitrenes • Nucleophilic Aromatic Substitution • Electrophilic Aromatic Substitution • Carbocations • Nucleophilic Aliphatic Substitution • Carbanions and Electrophilic Aliphatic Substitution • Elimination Reactions • Polar Addition Reactions • Cycloaddition Reactions • Molecular Rearrangements An experienced team of authors compile these reviews every year, so that the reader can rely on a continuing quality of selection and presentation.

Olefin Polymerization

Author : Walter Kaminsky
Publisher : Wiley-VCH
ISBN 13 : 9783527317424
Total Pages : 0 pages
Book Rating : 4.3/5 (174 download)

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Book Synopsis Olefin Polymerization by : Walter Kaminsky

Download or read book Olefin Polymerization written by Walter Kaminsky and published by Wiley-VCH. This book was released on 2006-08-18 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: With an enormous velocity, olefin polymerization has expanded to one of the most significant fields in polymers since the first industrial use about 50 years ago. In 2005, 100 million tons of polyolefins were produced - the biggest part was catalyzed by metallorganic compounds. The Hamburg Macromolecular Symposium 2005 with the title "Olefin Polymerization" involved topics such as new catalysts and cocatalysts, kinetics, mechanism and polymer reaction engineering, synthesis of special polymers, and characterization of polyolefins. The conference combined scientists from different disciplines to discuss latest research results of polymers and to offer each other the possibility of cooperation. This is reflected in this volume, which contains invited lectures and selected posters presented at the symposium.

Development of New Transition Metal Catalysts for C-N Bond Formation and Continuous Flow Processes for C-F Bond Formation

Author : Nathaniel Hamilton Park
Publisher :
ISBN 13 :
Total Pages : 391 pages
Book Rating : 4.:/5 (94 download)

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Book Synopsis Development of New Transition Metal Catalysts for C-N Bond Formation and Continuous Flow Processes for C-F Bond Formation by : Nathaniel Hamilton Park

Download or read book Development of New Transition Metal Catalysts for C-N Bond Formation and Continuous Flow Processes for C-F Bond Formation written by Nathaniel Hamilton Park and published by . This book was released on 2015 with total page 391 pages. Available in PDF, EPUB and Kindle. Book excerpt: The work presented in this dissertation addresses the development of new methodologies and processes to form carbon-nitrogen (C-N) and carbon-fluorine (C-F) bonds. The development of methods for the formation of C-N and C-F bonds are highly important to chemistry in general and find broad application in many different areas of research. With regard to C-N bond formation, the development of new nickel and palladium catalyst for C-N cross-coupling is presented. Finally, the development of a new process to enable the rapid preparation of aryl fluorides via the Balz-Schiemann reaction is explored. Chapter 1. Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates. A new air-stable nickel precatalyst for C-N cross-coupling is reported. The developed catalyst system displays a greatly improved substrate scope for C-N bond formation to include both a wide range of aryl and heteroaryl electrophiles and aryl, heteroaryl, and alkyl amines. The catalyst system is also compatible with weak base, allowing for the amination of substrates containing base-sensitive functional groups. Chapter 2. Design of New Ligands for the Palladium-Catalyzed Arylation of a- Branched Secondary Amines. In Pd-catalyzed C-N cross-coupling reactions, a-branched secondary amines are difficult coupling partners and often produce low yields of the desired product. To provide a robust method for accessing N-aryl a-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions. Chapter 3. Rapid Synthesis of Aryl Fluorides in Continuous Flow via the Balz- Schiemann Reaction. The synthesis of aryl fluorides (ArF) is of critical importance for the development of new and potent pharmaceuticals and agrochemicals. While there have been numerous and intense research efforts focused on developing new fluorination methods, the Balz-Schiemann reaction remains a valuable and efficient means of aryl C-F bond construction from a vast pool of available aryl amines. However, the harsh reaction conditions, modest yields, and often prohibitive safety concerns have limited the general application of this methodology. Here, we have developed a semi-flow process that enables safe handling of the potentially explosive aryl diazonium salt intermediates as well as improved yields of the desired aryl fluoride products. This process has been demonstrated on an array of different aryl and heteroaryl amine substrates containing a variety of different functional groups.

Mechanistic Studies on Transition Metal-Catalyzed C–H Activation Reactions Using Combined Mass Spectrometry and Theoretical Methods

Download Mechanistic Studies on Transition Metal-Catalyzed C–H Activation Reactions Using Combined Mass Spectrometry and Theoretical Methods PDF Online Free

Author : Gui-Juan Cheng
Publisher : Springer
ISBN 13 : 9811045216
Total Pages : 140 pages
Book Rating : 4.8/5 (11 download)

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Book Synopsis Mechanistic Studies on Transition Metal-Catalyzed C–H Activation Reactions Using Combined Mass Spectrometry and Theoretical Methods by : Gui-Juan Cheng

Download or read book Mechanistic Studies on Transition Metal-Catalyzed C–H Activation Reactions Using Combined Mass Spectrometry and Theoretical Methods written by Gui-Juan Cheng and published by Springer. This book was released on 2017-06-07 with total page 140 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis presents detailed mechanistic studies on a series of important C-H activation reactions using combined computational methods and mass spectrometry experiments. It also provides guidance on the design and improvement of catalysts and ligands. The reactions investigated include: (i) a nitrile-containing template-assisted meta-selective C-H activation, (ii) Pd/mono-N-protected amino acid (MPAA) catalyzed meta-selective C-H activation, (iii) Pd/MPAA catalyzed asymmetric C-H activation reactions, and (iv) Cu-catalyzed sp3 C-H cross-dehydrogenative-coupling reaction. The book reports on a novel dimeric Pd-M (M = Pd or Ag) model for reaction (i), which successfully explains the meta-selectivity observed experimentally. For reaction (ii), with a combined DFT/MS method, the author successfully reveals the roles of MPAA ligands and a new C-H activation mechanism, which accounts for the improved reactivity and high meta-selectivity and opens new avenues for ligand design. She subsequently applies ion-mobility mass spectrometry to capture and separate the [Pd(MPAA)(substrate)] complex at different stages for the first time, providing support for the internal-base model for reaction (iii). Employing DFT studies, she then establishes a chirality relay model that can be widely applied to MPAA-assisted asymmetric C-H activation reactions. Lastly, for reaction (iv) the author conducts detailed computational studies on several plausible pathways for Cu/O2 and Cu/TBHP systems and finds a reliable method for calculating the single electron transfer (SET) process on the basis of benchmark studies.

The Mizoroki-Heck Reaction

Author : Martin Oestreich
Publisher : John Wiley & Sons
ISBN 13 : 9780470716069
Total Pages : 608 pages
Book Rating : 4.7/5 (16 download)

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Book Synopsis The Mizoroki-Heck Reaction by : Martin Oestreich

Download or read book The Mizoroki-Heck Reaction written by Martin Oestreich and published by John Wiley & Sons. This book was released on 2009-02-11 with total page 608 pages. Available in PDF, EPUB and Kindle. Book excerpt: Exploring the importance of Richard F. Heck’s carbon coupling reaction, this book highlights the subject of the 2010 Nobel Prize in Chemistry for palladium-catalyzed cross couplings in organic synthesis, and includes a foreword from Nobel Prize winner Richard F. Heck. The Mizoroki-Heck reaction is a palladium-catalyzed carbon–carbon bond forming process which is widely used in organic and organometallic synthesis. It has seen increasing use in the past decade as chemists look for strategies enabling the controlled construction of complex carbon skeletons. The Mizoroki-Heck Reaction is the first dedicated volume on this important reaction, including topics on: mechanisms of the Mizoroki-Heck reaction intermolecular Mizoroki-Heck reactions focus on regioselectivity and product outcome in organic synthesis waste-minimized Mizoroki-Heck reactions intramolecular Mizoroki-Heck reactions formation of heterocycles chelation-controlled Mizoroki-Heck reactions the Mizoroki-Heck reaction in domino processes oxidative heck-type reactions (Fujiwara-Moritani reactions) Mizoroki-Heck reactions with metals other than palladium ligand design for intermolecular asymmetric Mizoroki-Heck reactions intramolecular enantioselective Mizoroki-Heck reactions desymmetrizing Mizoroki-Heck reactions applications in combinatorial and solid phase syntheses, and the development of modern solvent systems and reaction techniques the asymmetric intramolecular Mizoroki-Heck reaction in natural product total synthesis Several chapters are devoted to asymmetric Heck reactions with particular focus on the construction of otherwise difficult-to-obtain sterically congested tertiary and quaternary carbons. Industrial and academic applications are highlighted in the final section. The Mizoroki-Heck Reaction will find a place on the bookshelves of any organic or organometallic chemist. “I am convinced that this book will rapidly become the most important reference text for research chemists in academia and industry who seek orientation in the rapidly growing and – for the layman – confusing field described as the “’Mizoroki–Heck reaction’.” (Synthesis, March 2010)

Functionalization of Polyolefins

Author : T. C. Chung
Publisher : Academic Press
ISBN 13 : 9780121746513
Total Pages : 296 pages
Book Rating : 4.7/5 (465 download)

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Book Synopsis Functionalization of Polyolefins by : T. C. Chung

Download or read book Functionalization of Polyolefins written by T. C. Chung and published by Academic Press. This book was released on 2002-02-28 with total page 296 pages. Available in PDF, EPUB and Kindle. Book excerpt: Summarizes the significant experimental results on the functionalization of polyolefins and classifies them into several chemical methods. This book also provides information on the functional polyolefin materials. It covers: chemical approaches in the functionalization of polyolefins, and polyolefin materials and their potential applications.

Transition Metal Mediated Non-directed C-H Functionalization

Author : Joseph J. Gair
Publisher :
ISBN 13 : 9780438370395
Total Pages : 246 pages
Book Rating : 4.3/5 (73 download)

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Book Synopsis Transition Metal Mediated Non-directed C-H Functionalization by : Joseph J. Gair

Download or read book Transition Metal Mediated Non-directed C-H Functionalization written by Joseph J. Gair and published by . This book was released on 2018 with total page 246 pages. Available in PDF, EPUB and Kindle. Book excerpt: The structure and reactivity of organometallic species relevant to non-directed C- H activation and C-H functionalization are studied to inform the design of discrete pre- catalysts suitable for incorporation into supramolecular scaffolds. First, a study of transmetallation of hydrocarbyl ligands between transition metals demonstrates potential for dual-metal catalysis, in which one species cleaves C-H bonds and transfers the metallated fragment to a second metal suited for functionalization of the metal-carbon bond. Ligand modification of a rhodium (PNP) pincer complex gives rise to 100-fold rate enhancements toward non-directed C-H activation and this stoichiometric reactivity is leveraged to develop a catalytic method for non-directed C-H functionalization. During investigation of C-H activation with (PNP)Rh complexes, a heterobimetallic transition state analogue was isolated and characterized. Bonding analysis of the analogue demonstrates that the unusual geometry is supported by the same types of bonding interactions as those found in the putative transition state. Isolation and characterization of palladacycles coordinated by mono-protected amino acids (MPAA) reveals an unexpected MPAA-bridged di-palladium structure. Steady state kinetic analysis of Pd- MPAA catalyzed C-H functionalization, in particular the kinetic method of continuous variation, reveals that MPAA-bridged di-palladium complexes are responsible for MPAA- dependent rate acceleration and enantioinduction.

Visible Light Photocatalysis in Organic Chemistry

Author : Corey R.J. Stephenson
Publisher : John Wiley & Sons
ISBN 13 : 3527335609
Total Pages : 454 pages
Book Rating : 4.5/5 (273 download)

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Book Synopsis Visible Light Photocatalysis in Organic Chemistry by : Corey R.J. Stephenson

Download or read book Visible Light Photocatalysis in Organic Chemistry written by Corey R.J. Stephenson and published by John Wiley & Sons. This book was released on 2018-05-29 with total page 454 pages. Available in PDF, EPUB and Kindle. Book excerpt: Filling the need for a ready reference that reflects the vast developments in this field, this book presents everything from fundamentals, applications, various reaction types, and technical applications. Edited by rising stars in the scientific community, the text focuses solely on visible light photocatalysis in the context of organic chemistry. This primarily entails photoinduced electron transfer and energy transfer chemistry sensitized by polypyridyl complexes, yet also includes the use of organic dyes and heterogeneous catalysts. A valuable resource to the synthetic organic community, polymer and medicinal chemists, as well as industry professionals.

Arene Chemistry

Author : Jacques Mortier
Publisher : John Wiley & Sons
ISBN 13 : 1118754980
Total Pages : 992 pages
Book Rating : 4.1/5 (187 download)

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Book Synopsis Arene Chemistry by : Jacques Mortier

Download or read book Arene Chemistry written by Jacques Mortier and published by John Wiley & Sons. This book was released on 2015-11-30 with total page 992 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organized to enable students and synthetic chemists to understand and expand on aromatic reactions covered in foundation courses, the book offers a thorough and accessible mechanistic explanation of aromatic reactions involving arene compounds. • Surveys methods used for preparing arene compounds and their transformations • Connects reactivity and methodology with mechanism • Helps readers apply aromatic reactions in a practical context by designing syntheses • Provides essential information about techniques used to determine reaction mechanisms

Novel Metal- and Main Group-catalyzed Methods for Modulating Molecular Oxygenation

Author : Julian Colton Cooper
Publisher :
ISBN 13 :
Total Pages : 292 pages
Book Rating : 4.:/5 (114 download)

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Book Synopsis Novel Metal- and Main Group-catalyzed Methods for Modulating Molecular Oxygenation by : Julian Colton Cooper

Download or read book Novel Metal- and Main Group-catalyzed Methods for Modulating Molecular Oxygenation written by Julian Colton Cooper and published by . This book was released on 2019 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthetic methodologies frequently rely on oxygen functionality as a synthetic handle to enable structural modification of organic molecules; therefore, methods that enable new ways to modulate oxygen content in molecular structure facilitate structural diversification. This thesis details the development of catalytic methods affecting oxygen incorporation in organic molecules. These methods make use of fundamentally distinct strategies in bond activation to oxygenate and deoxygenate molecular architectures. First, a metal induced bond-weakening, dual-catalytic strategy was implemented to oxidize the benzylic positions of azaheterocycles. Coordination of a metal catalyst to the nitrogen lone pair is thought to induce weakening of proximal C-H bonds such that a radical catalyst with tunable chemoselectivity breaks this weakened bond. In the presence of an oxygen atmosphere, this leads to carbon-oxygen bond formation. This two-catalyst strategy is applied to the oxygenation of the benzylic positions of pharmaceutically relevant heterocycles, and is found to exhibit site selectivity for the electron poor azaheterocyclic positions, thereby addressing a longstanding challenge in catalytic C-H oxidation methods, which are typically selective for more electron-rich positions. Complementing metal catalyzed oxygenation, a main group-catalyzed method for deoxygenation is detailed. Geometrically distorted phosphorus compounds are shown to be competent catalysts for reductive 0-atom transfer, enabling the deoxygenation of nitroarenes and carbonyls, thereby realizing new reactivity for these functional groups. This main group catalysis renders nitro groups competent coupling partners for C-N bond formation, enabling cross coupling with an aryl boronic acid or anti-Markovnikov hydroamination with olefins. While catalytic 0-atom transfer with organophosphorus is well-studied, asymmetric variants remain limited. Advances in asymmetric carbonyl functionalization with distorted redoxactive phosphorus catalyst are presented, with the ultimate goal of gaining a greater understanding of the many factors that affect stereochemistry during these reactions.

Supported Catalysts and Their Applications

Author : David C Sherrington
Publisher : Royal Society of Chemistry
ISBN 13 : 1847551963
Total Pages : 282 pages
Book Rating : 4.8/5 (475 download)

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Book Synopsis Supported Catalysts and Their Applications by : David C Sherrington

Download or read book Supported Catalysts and Their Applications written by David C Sherrington and published by Royal Society of Chemistry. This book was released on 2007-10-31 with total page 282 pages. Available in PDF, EPUB and Kindle. Book excerpt: The need to improve both the efficiency and environmental acceptability of industrial processes is driving the development of heterogeneous catalysts across the chemical industry, including commodity, specialty and fine chemicals and in pharmaceuticals and agrochemicals. Drawing on international research, Supported Catalysts and their Applications discusses aspects of the design, synthesis and application of solid supported reagents and catalysts, including supported reagents for multi-step organic synthesis; selectivity in oxidation catalysis; mesoporous molecular sieve catalysts; and the use of Zeolite Beta in organic reactions. In addition, the two discrete areas of heterogeneous catalysis (inorganic oxide materials and polymer-based catalysts) that were developing in parallel are now shown to be converging, which will be of great benefit to the whole field. Providing a snapshot of the state-of-the-art in this fast-moving field, this book will be welcomed by industrialists and researchers, particularly in the agrochemicals and pharmaceuticals industries.

Investigations in Iron, Copper, and Palladium-catalyzed C-H Bond Functionalization

Author : Ly Dieu Tran
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (93 download)

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Book Synopsis Investigations in Iron, Copper, and Palladium-catalyzed C-H Bond Functionalization by : Ly Dieu Tran

Download or read book Investigations in Iron, Copper, and Palladium-catalyzed C-H Bond Functionalization written by Ly Dieu Tran and published by . This book was released on 2013 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metal-catalyzed functionalization of C-H bonds has been used as a powerful tool for the construction of C-C and C-heteroatom bonds. Within this dissertation, methods that allow functionalization of C-H bonds via iron and copper catalysis have been developed. Additionally, functionalization of sp3 C-H bonds in amino acid derivatives using auxiliary-assisted palladium-catalyzed methodology is also demonstrated. A method for iron-catalyzed alkylation of arenes and heterocycles containing acidic C-H bonds has been developed. Various heterocycles such as pyridine, furan, thiophene and electron deficient arenes can be coupled with both alkyl bromides and iodides. Magnesium amide base is required for the reaction. Similarly, the deprotonative dimerization of arenes and heterocycles can be effected in the presence of an iron catalyst. Thus, the method allows direct functionalization of arenes and heterocycles. Additionally, the use of an iron catalyst is an advantage compared with existing methods. Methods for copper-catalyzed direct sulfenylation and amination of sp2 C-H bonds have been developed. Using 8-aminoquinoline auxiliary and copper catalyst, ortho C-H bonds of benzoic acid amides can be sulfenylated by disulfides. The method provides an alternative, milder way for the preparation of aryl trifluoromethylsulfides. Furthermore, ortho C-H bonds of benzoic acid amides can be aminated by reaction with simple amines using 8-aminoquinoline directing group and a copper catalyst. Sulfenylation and amination of g-C-H bonds of benzyl amine derivatives using picolinic acid auxiliary were also demonstrated. Broad substrate scope, high regioselectivity, and good functional group tolerance were observed. The use of a copper catalyst and a removable directing group are significant improvements compared with the existing methods. Finally, a novel way for synthesis of non-natural amino acids via auxiliary-assisted, palladium-catalyzed C-H functionalization methodology was developed. Under palladium catalysis, 2-methyl thioaniline auxiliary allows the monoarylation of b-C-H bonds of alanine derivatives generating, after directing group removal, substituted phenylalanines. In contrast, using 8-aminoquinoline auxiliary, methylene groups in phenylalanine, leucine, and lysine derivatives can be arylated. Methods for alkylation and acetoxylation were also reported. The directing group can be removed without significant erosion of enantiomeric excess. The method provides a straight-forward way to synthesize non-natural amino acids from the chiral pool.