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Palladium Catalyzed Intramolecular Aminoalkylation Of Unactivated Alkenes For Synthesis Of Nitrogen Containing Heterocycles
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Book Synopsis Palladium-Catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes for Synthesis of Nitrogen-Containing Heterocycles by : Liu Ye
Download or read book Palladium-Catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes for Synthesis of Nitrogen-Containing Heterocycles written by Liu Ye and published by Open Dissertation Press. This book was released on 2017-01-26 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation, "Palladium-catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes for Synthesis of Nitrogen-containing Heterocycles" by Liu, Ye, 葉柳, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Palladium-catalyzed carboamination (simultaneous formation of C-N and C-C bonds from an olefin) has emerged as an efficient protocol for the synthesis of diversely functionalized N-heterocycles, which are widely displayed in natural products and pharmaceuticals. Compared with the well-documented aminoarylation, aminovinylation and aminoalkynylation, analogous aminoalkylation remains a challenge. This project aims at developing innovative strategies for aminoalkylation to construct a broad array of N-containing heterocycles. An efficient and general palladium-catalyzed intramolecular aminoalkylation of alkenyl aromatic α-halo acetamides with a wide substrate scope under mild conditions has been developed, yielding diverse dihydropyrroloindole derivatives of pharmaceutical interest. Preliminary mechanistic studies suggest that the reaction involves a Pd(0)/Pd(II) catalytic cycle, initiated by oxidative addition of α-halogen of amide with Pd(0) complex. The formation of an unprecedented four-membered-ring Pd(alkyl)amido complex is also supported by ESI-MS analysis. The synthetic utility of this aminoalkylation has been demonstrated by the synthesis of bioactive compounds A, B and C. Then the aminoalkylation reaction has been expanded to the more challenging alkenyl aliphatic α-halo acetamide substrates. This transformation features no requirement for air and moisture sensitive phosphine ligands and provides a straightforward access to a variety of bicyclic pyrrolizidine derivatives. Detailed mechanism studies support the hypothesis that the formation of a four-coordinate intermediate 3-IV is crucial for the realization of this transformation. An isotopic labeling experiment indicates that the aminopalladation proceeds through syn-insertion of alkene into Pd-N bond. The application of this aminoalkylation reaction to construct bicyclic isoxazolidines from α-halo oxy-acetamides has been explored. The reaction proceeds well at room temperature for α-iodo substrates. In addition, α-bromo and α-chloro substrates are also compatible, affording the desired products in good yields with moderate diastereoselectivity. The observation of different effects from externally added phosphine ligands indicates a distinct catalytic cycle, which may involve an initial aminopalladation followed by bimetallic transmetallation or oxidative addition. This tandem cyclization may offer a novel route to natural products and bioactive compounds containing this core. Finally, the enantioselective intramolecular aminoalkylation for the construction of chiral bicyclic isoxazolidines has been attempted. After screening of a variety of reaction parameters and a series of SPINOL-based ligands, a catalytic system has been disclosed, which utilizes 7 mol% Pd(TFA)2, 20 mol% (R)-Siphos-PE, 300 mol% sodium bromide and 100 mol% sodium carbonate. The desired product can be obtained in 70% yield with 60% enantiomeric excess. A general structure-activity-relationship (SAR) for SPINOL-based ligands is obtained, which provides a platform for further modification. DOI: 10.5353/th_b5610939 Subjects: Heterocyclic compounds - Synthesis Transition metal catalysts
Book Synopsis Palladium-catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes for Synthesis of Nitrogen-containing Heterocycles by : 葉柳
Download or read book Palladium-catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes for Synthesis of Nitrogen-containing Heterocycles written by 葉柳 and published by . This book was released on 2015 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Palladium Assisted Synthesis of Heterocycles by : Navjeet Kaur
Download or read book Palladium Assisted Synthesis of Heterocycles written by Navjeet Kaur and published by CRC Press. This book was released on 2019-05-01 with total page 432 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a compilation of the recent applications of palladium catalysts in organic synthesis. The book demonstrates that it is a highly dynamic research field. This methodology has emerged as a powerful tool for the efficient and chemoselective synthesis of heterocyclic molecules. In the past few years, several strategies have been pointed out to pursue more efficient, sustainable, and environment friendly chemical processes. Among those strategies, catalysis and the design of new processes that avoid the use of toxic reagents have been the focus of intense research.
Book Synopsis Palladium-Catalyzed Oxidative Cascade Cyclizations Via C-N/C-C Formation for Synthesis of Nitrogen Heterocycles by : Wei Du
Download or read book Palladium-Catalyzed Oxidative Cascade Cyclizations Via C-N/C-C Formation for Synthesis of Nitrogen Heterocycles written by Wei Du and published by . This book was released on 2017-01-27 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation, "Palladium-catalyzed oxidative cascade cyclizations via C-N/C-C formation for synthesis of nitrogen heterocycles" by Wei, Du, 杜玮, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Abstract of thesis entitled PALLADIUM-CATALYZED OXIDATIVE CASCADE CYCLIZATIONS VIA C-N/C-C FORMATION FOR SYNTHESIS OF NITROGEN HETEROCYCLES submitted by Du Wei for the Degree of Doctor of Philosophy at The University of Hong Kong in May 2014 Pd(II)-catalyzed oxidative amination of alkenes is a versatile method to construct N-containing heterocycles which are found in many biologically active synthetic targets, including natural products and pharmaceuticals. Considering the efficiency of the cascade reaction, we have employed this protocol to synthesize nitrogen heterocycles (including chiral ones) via Pd(II)-catalyzed C-N/C-C bond formation. We have developed a highly efficient enantioselective method for oxidative cascade cyclization of acrylamides tethered alkene using Pd(TFA) /diPh-pyrox as catalyst under a mild aerobic condition (Scheme 1). A series of pyrrolizidine derivatives, such as 2.4a, 2.2h, and 2.2n, have been synthesized in good yields and excellent enantioselectivity. The mechanism study has indicated that the cyclization reaction proceeded through both trans-/cis-aminopalladation (AP) with a ratio of ca. 3:1 (Scheme 2). Besides, we have found that some factors, including the counterions of Pd(II) complexes, the electronic density of the isolated double bond and the steric bulkiness of ligands, affect the stereochemical selectivity in the aminopalladation step. This study has important implications for designing new catalyst systems for enantioselective Pd-catalyzed oxidative amination reactions. We have also disclosed the first enantioselective Pd(II)-catalyzed oxidative aminoarylation reaction (Scheme 3). The reactions were carried out with Pd(OAc) /β-ICD as catalyst to synthesize indoline derivatives, such as 3.2a, 3.2b and 3.2i, in moderate to good yields with moderate enantioselectivity. Base on previous successful cascade reactions of aminopalladation/C(sp )-H functionalization, we have developed a palladium (II)-catalyzed oxidative cascade aminoalkylation via aminopalladation/C(sp )-H activation for divergent synthesis of three-membered-ring (i.e. 4.2ag, 4.2an and 4.2ar) or five-membered-ring (i.e. 4.3aa, 4.3ad and 4.3bs) fused indolines (Scheme 4). The benzylic C-H and the C-H at -position of anilides can be selectively activated under different reaction conditions. 3 This is the first example of palladium catalyzed C(sp )-H activation without employment of prefunctionalized reagents (halogenated or boron-containing reagents) and directing groups, representing a green and economic protocol for construction of N-containing heterocycles. Scheme 1 Scheme 2 Scheme 3 Scheme 4 DOI: 10.5353/th_b5312312 Subjects: Heterocyclic compounds - Synthesis Organopalladium compounds
Book Synopsis Transition Metal-catalyzed Preparation and Functionalization of Nitrogen-containing Heterocycles by : Malcolm P. Huestis
Download or read book Transition Metal-catalyzed Preparation and Functionalization of Nitrogen-containing Heterocycles written by Malcolm P. Huestis and published by . This book was released on 2009 with total page 148 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Development and Application of Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions by : Seble-Hiwot Teshome Wagaw
Download or read book Development and Application of Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions written by Seble-Hiwot Teshome Wagaw and published by . This book was released on 1999 with total page 280 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Palladium(II) Catalyzed Intramolecular Hydroamination of 1,3-dienes by : Justin M. Pierson
Download or read book Palladium(II) Catalyzed Intramolecular Hydroamination of 1,3-dienes written by Justin M. Pierson and published by . This book was released on 2012 with total page 26 pages. Available in PDF, EPUB and Kindle. Book excerpt: A highly regioselective palladium catalyzed intramolecular hydroamination of substituted 1,3-dienes was achieved to create diverse nitrogen containing heterocycles. Hydroamination of 1,3-dienes goes in high yields, is selective for 1,2 addition and is suitable for a wide variety of nitrogen protecting groups. Insight to the mechanism of 1,3-diene hydroamination was accomplished by isolating a crucial palladium allyl complex.
Book Synopsis Rhodium Catalysis by : Carmen Claver
Download or read book Rhodium Catalysis written by Carmen Claver and published by Springer. This book was released on 2017-12-15 with total page 291 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 abbrev iated as Top Organomet Chem and cited as a journal.
Book Synopsis Organotransition Metal Chemistry: From Bonding to Catalysis by : John F. Hartwig
Download or read book Organotransition Metal Chemistry: From Bonding to Catalysis written by John F. Hartwig and published by . This book was released on 2010-02-10 with total page 1172 pages. Available in PDF, EPUB and Kindle. Book excerpt: Based on Collman et al.'s best-selling classic book, Principles and Applications of Organotransition Metal Chemistry, Hartwig's text consists of new or thoroughly updated and restructured chapters and provides an in-depth view into mechanism, reaction scope, and applications. It covers the most important developments in the field over the last twenty years with great clarity with a selective, but thorough and authoritative coverage of the fundamentals of organometallic chemistry, the elementary reactions of these complexes, and many catalytic processes occurring through organometallic intermediates, making this the Organotransition Metal Chemistry text for a new generation of scientists.
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)
Book Synopsis Heterocyclic N-Oxides by : Oleg V. Larionov
Download or read book Heterocyclic N-Oxides written by Oleg V. Larionov and published by Springer. This book was released on 2017-07-12 with total page 163 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.
Book Synopsis Applications of Transition Metal Catalysis in Drug Discovery and Development by : Matthew L. Crawley
Download or read book Applications of Transition Metal Catalysis in Drug Discovery and Development written by Matthew L. Crawley and published by John Wiley & Sons. This book was released on 2012-05-14 with total page 386 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book focuses on the drug discovery and development applications of transition metal catalyzed processes, which can efficiently create preclinical and clinical drug candidates as well as marketed drugs. The authors pay particular attention to the challenges of transitioning academically-developed reactions into scalable industrial processes. Additionally, the book lays the groundwork for how continued development of transition metal catalyzed processes can deliver new drug candidates. This work provides a unique perspective on the applications of transition metal catalysis in drug discovery and development – it is a guide, a historical prospective, a practical compendium, and a source of future direction for the field.
Book Synopsis Sustainable Organic Synthesis by : Dr Stefano Protti
Download or read book Sustainable Organic Synthesis written by Dr Stefano Protti and published by Royal Society of Chemistry. This book was released on 2021-10-29 with total page 602 pages. Available in PDF, EPUB and Kindle. Book excerpt: Recent years have seen huge growth in the area of sustainable chemistry. In order to meet the chemical needs of the global population whilst minimising impacts on health and the environment it is essential to keep reconsidering and improving synthetic processes. Sustainable Organic Synthesis is a comprehensive collection of contributions, provided by specialists in Green Chemistry, covering topics ranging from catalytic approaches to benign and alternative reaction media, and innovative and more efficient technologies.
Book Synopsis Carbon-carbon Bond Formation by : Robert L. Augustine
Download or read book Carbon-carbon Bond Formation written by Robert L. Augustine and published by CRC Press. This book was released on 1979-04-01 with total page 480 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Ecocatalysis written by Claude Grison and published by Elsevier. This book was released on 2015-08-19 with total page 102 pages. Available in PDF, EPUB and Kindle. Book excerpt: Reconquest of biodiversity; remediation of degraded and anthropic areas, prevention of environmental health risks; eco-innovation; Green industry ... The current French ambitions are closely related to an interdisciplinary approach to scientific ecology, all of which participate in the expected industrial renewal.Ecocatalysis explores the unusual combination of phytotechnologies adapted to pollution, ecological rehabilitation of polluted sites and enhancement of these processes through innovative green chemistry, all of which contribute to the development of scientific priorities; economic, ecological innovation and current environmental, of biomass conversion and transition from fossil fuels to renewable.
Book Synopsis Practical Synthetic Organic Chemistry by : Stéphane Caron
Download or read book Practical Synthetic Organic Chemistry written by Stéphane Caron and published by John Wiley & Sons. This book was released on 2020-02-05 with total page 850 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a hands-on guide for the organic chemist. Focusing on the most reliable and useful reactions, the chapter authors provide the information necessary for a chemist to strategically plan a synthesis, as well as repeat the procedures in the laboratory. Consolidates all the key advances/concepts in one book, covering the most important reactions in organic chemistry, including substitutions, additions, eliminations, rearrangements, oxidations, reductions Highlights the most important reactions, addressing basic principles, advantages/disadvantages of the methodology, mechanism, and techniques for achieving laboratory success Features new content on recent advances in CH activation, photoredox and electrochemistry, continuous chemistry, and application of biocatalysis in synthesis Revamps chapters to include new and additional examples of chemistry that have been demonstrated at a practical scale
Book Synopsis Green Oxidation in Organic Synthesis by : Ning Jiao
Download or read book Green Oxidation in Organic Synthesis written by Ning Jiao and published by John Wiley & Sons. This book was released on 2019-09-30 with total page 531 pages. Available in PDF, EPUB and Kindle. Book excerpt: A valuable introduction to green oxidation for organic chemists interested in discovering new strategies and new reactions for oxidative synthesis Green Oxidation in Organic Synthesis provides a comprehensive introduction and overview of chemical preparation by green oxidative processes, an entry point to the growing journal literature on green oxidation in organic synthesis. It discusses both experimental and theoretical approaches for the study of new catalysts and methods for catalytic oxidation and selective oxidation. The book highlights the discovery of new reactions and catalysts in recent years, discussing mechanistic insights into the green oxidative processes, as well as applications in organic synthesis with significant potential to have a major impact in academia and industry. Chapters are organized according to the functional groups generated in the reactions, presenting interesting achievements for functional group formation by green oxidative processes with O2, H2O2, photocatalytic oxidation, electrochemical oxidation, and enzymatic oxidation. The mechanisms of these novel transformations clearly illustrated. Green Oxidation in Organic Synthesis will serve as an excellent reference for organic chemists interested in discovering new strategies for oxidative synthesis which address the priorities of green and sustainable chemistry.
