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Metal Free Catalysis Using Boron Based Systems From Designed Frustrated Lewis Pairs To Boranes
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Book Synopsis Metal-free catalysis using boron-based systems: from designed frustrated Lewis Pairs to boranes by : Julien Légaré Lavergne
Download or read book Metal-free catalysis using boron-based systems: from designed frustrated Lewis Pairs to boranes written by Julien Légaré Lavergne and published by . This book was released on 2021 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Résumé en anglais
Book Synopsis Frustrated Lewis Pairs by : J. Chris Slootweg
Download or read book Frustrated Lewis Pairs written by J. Chris Slootweg and published by Springer Nature. This book was released on 2020-11-22 with total page 404 pages. Available in PDF, EPUB and Kindle. Book excerpt: This volume highlights the latest research in frustrated Lewis pair (FLP) chemistry and its applications. The contributions present the recent developments of the use of FLPs in asymmetric catalysis, polymer synthesis, homogeneous and heterogeneous catalysis, as well as demonstrating their use as a pedagogical tool. The book will be of interest to researchers in academia and industry alike.
Book Synopsis Primer in Frustrated Lewis Pair Hydrogenation by : Douglas Stephan
Download or read book Primer in Frustrated Lewis Pair Hydrogenation written by Douglas Stephan and published by Royal Society of Chemistry. This book was released on 2021-11-17 with total page 248 pages. Available in PDF, EPUB and Kindle. Book excerpt: Written for senior undergraduate and graduate students, as well as those chemists unfamiliar with “frustrated Lewis pairs (FLPs)”, this text serves as an introduction to the both the concept and application of FLPs in hydrogenation catalysis. The book begins by setting the stage as it was around the turn of the century. While the dramatic impacts of catalysis were undeniable, there was dependence of such technologies on transition metal chemistry. Contrastingly, the chemistry of main group elements was dominated by Lewis acid-base behavior. However, these perceptions were altered with the discovery of the ability of “frustrated Lewis pairs (FLPs)” to activate dihydrogen. The basic features, and mechanisms of action of these unique main group systems are chronicled, while the evolution of the initial findings to applications in catalytic hydrogenation is discussed. A subsequent chapter focuses on the breadth of organic substrates for which borane based FLP hydrogenations are effective. This is furthered with a chapter on the metal-free enantioselective reductions. FLP chemistry is not limited to systems involving boranes and this book also catalogues a range of FLP hydrogenation catalysts involving elements from across the periodic table. The final chapter in the book describes other directions of interest where the application of the concept of FLPs hydrogenation are beginning to emerge. Ideal for course use and self study, this book provides synthetic chemists with a fresh, expert introduction to the field. The reader will be left recognizing that hydrogenation catalysts is a domain no longer limited to transition metals.
Book Synopsis Boron-based Lewis Acids by : Jolie Lam
Download or read book Boron-based Lewis Acids written by Jolie Lam and published by . This book was released on 2020 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: A rapid development of metal-free, main group compounds for small molecule activation and as hydrogenation catalysts was triggered after the disclosure of H2 activation by sterically hindered Lewis acids and bases over a decade ago. The combination of a Lewis acid and base with unquenched reactivity was later coined as a "frustrated Lewis pair" (FLP). In this research, boron-based Lewis acids were studied for their application as catalysts in FLP chemistry, with an emphasis on exploring the production of chiral FLPs and intramolecular FLPs. In the exploration towards enantioselective catalysis, 3,5-bicyclic aryl piperidines were synthetically modified to produce B/N FLPs and were shown to activate dihydrogen, demonstrating the potential for expanding chiral FLP templates beyond the typical chiral ligands used in transition metal complexes. Chiral borenium cations were generated from different families of carbene-borane adducts, in which their chirality resides on either the carbene or the borane. Catalytic studies found that they were able to effect imine reduction without epimerisation of the resulting chiral amine, and the reactivity and enantioselectivity of these cations were found to be inversely proportional to steric demands. In the exploration towards a cationic intramolecular FLP, a borenium cation with a pendant phosphine was synthesized through hydroboration of a phosphinoalkene with an isolable B-H borenium cation, and its FLP reactivity was investigated. Finally, initial efforts towards the production of a bisborane-carbene as a tri-functionalized FLP were documented.
Book Synopsis Frustrated Lewis Pairs II by : Gerhard Erker
Download or read book Frustrated Lewis Pairs II written by Gerhard Erker and published by Springer. This book was released on 2013-12-12 with total page 321 pages. Available in PDF, EPUB and Kindle. Book excerpt: Frustrated Lewis Pairs: From Dihydrogen Activation to Asymmetric Catalysis, by Dianjun Chen, Jürgen Klankermayer Coexistence of Lewis Acid and Base Functions: A Generalized View of the Frustrated Lewis Pair Concept with Novel Implications for Reactivity, by Heinz Berke, Yanfeng Jiang, Xianghua Yang, Chunfang Jiang, Subrata Chakraborty, Anne Landwehr New Organoboranes in "Frustrated Lewis Pair" Chemistry, by Zhenpin Lu, Hongyan Ye, Huadong Wang Paracyclophane Derivatives in Frustrated Lewis Pair Chemistry, by Lutz Greb, Jan Paradies Novel Al-Based FLP Systems, by Werner Uhl, Ernst-Ulrich Würthwein N-Heterocyclic Carbenes in FLP Chemistry, by Eugene L. Kolychev, Eileen Theuergarten, Matthias Tamm Carbon-Based Frustrated Lewis Pairs, by Shabana Khan, Manuel Alcarazo Selective C-H Activations Using Frustrated Lewis Pairs. Applications in Organic Synthesis, by Paul Knochel, Konstantin Karaghiosoff, Sophia Manolikakes FLP-Mediated Activations and Reductions of CO2 and CO, by Andrew E. Ashley, Dermot O’Hare Radical Frustrated Lewis Pairs, by Timothy H. Warren and Gerhard Erker Polymerization by Classical and Frustrated Lewis Pairs, by Eugene Y.-X. Chen Frustrated Lewis Pairs Beyond the Main Group: Transition Metal-Containing Systems, by D. Wass Reactions of Phosphine-Boranes and Related Frustrated Lewis Pairs with Transition Metal Complexes, by Abderrahmane Amgoune, Ghenwa Bouhadir, Didier Bourissou
Book Synopsis Future prospects in boron chemistry: new boron compounds and Lewis acids for catalysis and materials science by : Guillaume Berionni
Download or read book Future prospects in boron chemistry: new boron compounds and Lewis acids for catalysis and materials science written by Guillaume Berionni and published by OAE Publishing Inc.. This book was released on 2021-09-23 with total page 6 pages. Available in PDF, EPUB and Kindle. Book excerpt: Boron-containing compounds have a wide range of structures and rich and multifaceted reactivity patterns. As a result, these compounds are being increasingly used in organometallic, supramolecular, organic and inorganic chemistry, as well as in catalysis and materials science. This perspective describes recent ground-breaking studies and their implications for the future development of new catalysts and materials containing one or several trivalent boron atoms.
Book Synopsis Frustrated Lewis Pairs I by : Gerhard Erker
Download or read book Frustrated Lewis Pairs I written by Gerhard Erker and published by Springer. This book was released on 2014-07-08 with total page 354 pages. Available in PDF, EPUB and Kindle. Book excerpt: Discovery of Frustrated Lewis Pairs: Intermolecular FLPs for Activation of Small Molecules, by Douglas W. Stephan Intramolecular Frustrated Lewis Pairs: Formation and Chemical Features, by Gerald Kehr, Sina Schwendemann, Gerhard Erker Frustrated Lewis Pair Mediated Hydrogenations, by Douglas W. Stephan, Gerhard Erker Amine-Borane Mediated Metal-Free Hydrogen Activation and Catalytic Hydrogenation, by Victor Sumerin, Konstantin Chernichenko, Felix Schulz, Markku Leskelä, Bernhard Rieger, Timo Repo Hydrogen Activation by Frustrated Lewis Pairs: Insights from Computational Studies, by Tibor András Rokob, Imre Pápai Quantum Chemistry of FLPs and Their Activation of Small Molecules: Methodological Aspects, by Birgitta Schirmer, Stefan Grimme Computational Design of Metal-Free Molecules for Activation of Small Molecules, Hydrogenation, and Hydroamination, by Zhi-Xiang Wang, Lili Zhao, Gang Lu, Haixia Li, Fang Huang Computational Studies of Lewis Acidity and Basicity in Frustrated Lewis Pairs, by Thomas M. Gilbert Solid-State NMR as a Spectroscopic Tool for Characterizing Phosphane - Borane Frustrated Lewis Pairs, by Thomas Wiegand, Hellmut Eckert, Stefan Grimme
Book Synopsis Cooperative Reactivity of Boron-Containing Molecules and Lewis Bases for Metal Free Catalysis by : Marc-André Légaré
Download or read book Cooperative Reactivity of Boron-Containing Molecules and Lewis Bases for Metal Free Catalysis written by Marc-André Légaré and published by . This book was released on 2015 with total page 210 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metal catalysis is currently ubiquitous in all sectors of the chemical industry. The reactions it enables allow the production of countless useful chemicals. In the field of organic synthesis alone, the impact and development of catalytic reactions have been recognized several times by the award of Nobel prizes. The use of transition metals for catalysis, however, suffers from several drawbacks that include their high cost, their rarity and their potential toxicity and environmental impact. National and international agencies, as a matter of fact, regulate the trace amounts of residual metal that can be present in many end products. For this reason, there is great interest in discovering alternative catalysts produced from earth-abundant, nontoxic and inexpensive elements. Boron, as a light element of the main group, follows these criteria. The reactivity of organoboron compounds, however, is very different from that of organometallic complexes, and less adapted to typical catalytic process. For this reason, new concepts and new reactions have to be developed in order to introduce boron to the world of catalysis. In order to discover and develop novel ideas towards the design of boron catalysts, we have studied different instances in which Lewis bases influence the reactivity of boron compounds. We hypothesized that the combination of an organoborane and a Lewis base could achieve reactions that would be impossible for the separate units to accomplish. In a first case study, we have investigated in depth the reactivity of neutral adducts of borabenzene towards Lewis bases. We have found that, contrary to usual formulations, borabenzene, under the influence of a Lewis base, reacts as a nucleophile rather than an electrophile. The properties and reactivity of a great number of borabenzene compounds have been studied computationally and experimentally in a work that will be presented in this dissertation. Next, we have studied the reduction of carbon dioxide catalyzed by ambiphilic organoboron compounds. We describe new modes of coordination for boranes with Lewis bases and the application of these interactions to the reduction of CO2 to methanol derivatives. Finally, the culmination of our research efforts is shown as the rational development of a metal-free ambiphilic catalyst for the C-H bond activation and borylation of heteroarenes. In this dissertation, we describe the process by which we designed and implemented this catalytic reaction, as well as the specifics of the system.
Book Synopsis Synthesis of Boron, Silicon, and Phosphorus Lewis Acids and Frustrated Lewis Pair Complexes for C by : Ian Robert Faulkner Mallov
Download or read book Synthesis of Boron, Silicon, and Phosphorus Lewis Acids and Frustrated Lewis Pair Complexes for C written by Ian Robert Faulkner Mallov and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The recent proliferation of main group catalysts and stoichiometric reagents useful in effecting transformations of organic molecules has been augmented by development of the chemistry of frustrated Lewis pairs (FLPs). In seeking to both complement and emulate the reactivity of transition metal catalysts, both the synthesis of new Lewis acids and FLPs and the discovery of new reactivity with organic substrates has been explored. Boron Lewis acids such as B(C6F5)3 and electrophilic borenium cations are among the most commonly employed main group catalysts, particularly for the hydrogenation of unsaturated bonds. The first chapter of this thesis details explorations in modulating the Lewis acidity of neutral and cationic boron electrophiles by tuning phosphinimine and phosphine-amine ligands. A family of compounds featuring a P-N-B motif are presented. In seeking to broaden the range of main group catalysts, phosphorus Lewis acids have been explored. The third and fourth chapters presented herein detail the synthesis and catalytic activity of electrophilic phosphonium cations (EPCs). Synthesis of a chloride-substituted dication, and ferrocenyl-based mono- and dications are described, with a particular emphasis on their catalytic activity in the deoxygenation of ketones. The fifth chapter details the synthesis of phosphorus cations which attempt to model intermediates in EPC-mediated catalysis. Silylium cations are strongly fluorophilic and have previously been shown to cleave aliphatic C-F bonds. The final chapter presents examples of silylium cations in combination with weak phosphine Lewis bases for the selective cleavage of one C-F bond of an aryl-CF3 functionality. The FLP-captured PhCF2 is then converted to PhCF2H, completing a formal hydrodefluorination process of PhCF3 to PhCF2H. Analogous reactivity is observed with aryl-CF2 compounds.
Book Synopsis Ruthenium-Based Hydrogenation and Frustrated Lewis Pair Chemistry by : Louie Fan
Download or read book Ruthenium-Based Hydrogenation and Frustrated Lewis Pair Chemistry written by Louie Fan and published by . This book was released on 2018 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Since the discovery of catalytic hydrogenation, the field of transition metal-based hydrogenation catalysis has grown significantly. Recently, main group systems have demonstrated the capability to perform some of the same catalytic processes. Frustrated Lewis pairs (FLP), the combination of sterically encumbered Lewis acids and Lewis bases, are able to activate a variety of small molecules. The research presented in this thesis investigates main group and transition metal-based catalytic hydrogenation, as well as stoichiometric transformations with main group systems. A variety of ruthenium N-heterocyclic carbene (NHC) complexes were generated with polyethylene glycol (PEG) on the NHC to impart water-solubility. These hydrogenation catalysts were used to hydrogenate nitrile butadiene rubber (NBR) to hydrogenated nitrile butadiene rubber (HNBR). The PEG lengths had minimal effect on the conversion of NBR in solution phase. For the hydrogenation of NBR latex, a correlation was observed between the PEG length and the activity. A family of phosphinimines with different steric and electronic properties was synthesized from the Staudinger reaction between alkynyl-phosphines and azido-phosphine-boranes. Cyclization of these products can be induced thermally or by the addition of catalytic amounts of B(C6F5)3. Upon cyclization, a net trans-hydroboration was observed on the exocyclic alkene. A novel geminal boron-sulfur FLP was synthesized from the hydroboration of sulfur-alkynes. These systems demonstrated FLP-type chemistry such as the activation of terminal alkynes. Interestingly, the frustration was a result of the steric conflict between the tert-butyl substituent on the carbon and the p-tolyl substituent on the Lewis basic sulfur. This FLP-type reactivity can altered upon isomerization of the complex, forming the classical Lewis pair adduct. Finally, metal-free transformation of 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one was investigated. The Lewis acid B(C6F5)3 was shown to catalytically hydrogenate the allyl functionality of the substrate, as well as catalytic hydrosilylation of the conjugated alkene.
Book Synopsis Transition Metal Complexes and Main Group Frustrated Lewis Pairs for Stoichiometric and Catalytic P-P and H-H Bond Activation by : Stephen Joseph Geier
Download or read book Transition Metal Complexes and Main Group Frustrated Lewis Pairs for Stoichiometric and Catalytic P-P and H-H Bond Activation written by Stephen Joseph Geier and published by . This book was released on 2010 with total page 328 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis The Synthesis and Reactivity of Main Group Heterocycles Via Frustrated Lewis Pair Chemistry by : Lauren Elizabeth Longobardi
Download or read book The Synthesis and Reactivity of Main Group Heterocycles Via Frustrated Lewis Pair Chemistry written by Lauren Elizabeth Longobardi and published by . This book was released on 2017 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Combinations of sterically encumbered Lewis acids and bases, now referred to as a frustrated Lewis pair (FLP), have been shown to have a rich and diverse chemistry. Their advent led to the development of hydrogenation catalysis and other important transformations based on metal-free systems. This thesis investigates the chemistry of main group heterocycles, specifically those bearing phosphorus and/or boron atoms, within the realm of frustrated Lewis pair chemistry. Investigations of nitrogen Lewis bases included bulky anilines substituted with para-methoxy groups, which were found to undergo a tandem aromatic hydrogenation/transannulation reaction to yield bicyclic ammonium hydridoborate salts. Alkenyl- and alkynyl-tethered N-heterocycles were found to undergo intramolecular ring closure across the C-C -bond when treated with B(C6F5)3. Frustrated Lewis pairs were found to undergo 1,3-addition to N-sulfinylamines, which generated phosphinimine-borane and phosphinimine-alane adducts of sulfur monoxide. The activated species were found to oxidize triphenylphosphine and transfer sulfur monoxide to Wilkinson's complex and N-heterocyclic carbenes. Triphosphabenzene was shown to activate H2 independently, and the mechanism of this reaction was investigated. Phosphaalkynes did not react with prototypical phosphine-borane FLPs, however they were amenable to hydroboration with Piers' borane, which resulted in an unexpected regiochemical outcome. The reactivity of the dimeric P2B2 heterocycles was examined. Aliphatic ketones were demonstrated to undergo stoichiometric reduction to the corresponding borinic esters when exposed to one equivalent of B(C6F5)3 and H2. This methodology was applied to polycyclic aromatic diones, which resulted in formation of neutral borocyclic radicals. The chemical properties of the radicals were examined, and their reactivity with phosphorus, carbon, and nitrogen nucleophiles was explored.
Book Synopsis Valence and the Structure of Atoms and Molecules by : Gilbert Newton Lewis
Download or read book Valence and the Structure of Atoms and Molecules written by Gilbert Newton Lewis and published by . This book was released on 1923 with total page 184 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Organometallic Chemistry by : Ian Fairlamb
Download or read book Organometallic Chemistry written by Ian Fairlamb and published by Royal Society of Chemistry. This book was released on 2017-07-25 with total page 171 pages. Available in PDF, EPUB and Kindle. Book excerpt: With the increase in volume, velocity and variety of information, researchers can find it difficult to keep up to date with the literature in their field. This interdisciplinary field has the potential to provide answers to problems and challenges faced in catalysis, synthetic organic chemistry and the development of therapeutic agents and new materials. Providing an invaluable volume, Organometallic Chemistry Volume 41 contains analysed, evaluated and distilled information on the latest in organometallic chemistry research including developments and applications of Lewis acidic boron reagents, masked low-coordinate main group species in synthesis and the diiron centre.
Book Synopsis Organosilicon Chemistry by : Tamejiro Hiyama
Download or read book Organosilicon Chemistry written by Tamejiro Hiyama and published by John Wiley & Sons. This book was released on 2020-02-18 with total page 566 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides a unique summary of important catalytic reactions in the presence of silicon A must-have for all synthetic chemists, this book summarizes all of the important developments in the application of organosilicon compounds in organic synthesis and catalysis. Edited by two world leaders in the field, it describes different approaches and covers a broad range of reactions, e.g. catalytic generation of silicon nucleophiles, Si-H Bond activation, C-H bond silylation, silicon-based cross-coupling reactions, and hydrosilylation in the presence of earth-abundant metals. In addition to the topics covered above, Organosilicon Chemistry: Novel Approaches and Reactions features chapters that look at Lewis base activation of silicon Lewis acids, silylenes as ligands in catalysis, and chiral silicon molecules. -The first book about this topic in decades, covering a broad range of reactions -Covers new approaches and novel catalyst systems that have been developed in recent years -Written by well-known, international experts in the areas of organometallic silicon chemistry and organosilicon cross-coupling reactions Organosilicon Chemistry: Novel Approaches and Reactions is an indispensable source of information for synthetic chemists in academia and industry, working in the field of organic synthesis, catalysis, and main-group chemistry.
Book Synopsis Activation of Small Molecules by : William B. Tolman
Download or read book Activation of Small Molecules written by William B. Tolman and published by John Wiley & Sons. This book was released on 2006-12-13 with total page 382 pages. Available in PDF, EPUB and Kindle. Book excerpt: The first to combine both the bioinorganic and the organometallic view, this handbook provides all the necessary knowledge in one convenient volume. Alongside a look at CO2 and N2 reduction, the authors discuss O2, NO and N2O binding and reduction, activation of H2 and the oxidation catalysis of O2. Edited by the highly renowned William Tolman, who has won several awards for his research in the field.
Book Synopsis Early Main Group Metal Catalysis by : Sjoerd Harder
Download or read book Early Main Group Metal Catalysis written by Sjoerd Harder and published by John Wiley & Sons. This book was released on 2020-04-06 with total page 400 pages. Available in PDF, EPUB and Kindle. Book excerpt: Early Main Group Metal Catalysis gives a comprehensive overview of catalytic reactions in the presence of group 1 and group 2 metals. Chapters are ordered to reaction type, contain educational elements and deal with concepts illustrated by examples that cover the main developments. After a short introduction on polar organometallic chemistry and synthesis of early main group metal complexes, a variety of catalytic reactions are described, e.g. polymerization of alkenes, hydroamination and phosphination reactions, hydrosilylation, hydroboration and hydrogenation catalysis, as well as enantioselective and Lewis-acid catalysis. The book addresses organic chemists and researchers in industry interested in the state-of-the-art and new possibilities of early main group metal catalysis as well as newcomers to the field. Written by a team of leaders in the field, it is a very welcome addition to the area of main group metal chemistry, and to the field of catalysis.
