Chemo-, Regio-, and Diastereoselective C-C and C-O Bond Formation Via Transition Metal Catalysis PDF Download
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Author: Nusrah Hussain
Publisher:
ISBN:
Category :
Languages : en
Pages : 596
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Book Description
The efficient stereoselective formation of C-C and C-O bonds remains a critical challenge in organic chemistry. The level difficulty of these bond formations increases dramatically when regio-, diastereo-, and chemoselectivity issues are present. In efforts to address such challenges, this thesis summarizes three successful strategies to develop highly stereoselective C-C and C-O bond formation reactions: 1) the first strategy outlines the direct metallation and subsequent chemo- and regioselective cross-coupling of benzylic sp3-hybridized C-H bonds (pKa values >34) to form C- bonds via palladium catalyzed deprotonative cross-coupling process (DCCP), 2) the second strategy outlines the application of 1,1-heterobimetallic borozinc reagents in the diastereoselective C- bond-forming reactions, and 3) the third strategy outlines the use of transition metal-catalysis in the highly chemo- and diastereoselective C-O bond formation via vanadium catalyzed directed epoxidation. Chapters 1 and 2 summarize a program that we have recently initiated in our laboratory known as deprotonative cross-coupling process (DCCP). DCCP is the reversible in situ deprotonation of weakly acidic sp3-hybridized C-H bonds under mild conditions, which are then catalytically cross-coupled with aryl electrophiles under palladium catalysis. Chapters 3 and 4 summarize the potential usefulness of 1-alkenyl-l,l-heterobimetallics in the stereoselective C-C bond formations in organic synthesis. Our group reported a practical generation of 1,1-heterobimetallics from air-stable B(pin)-substituted alkynylboronate esters and demonstrated their utility in a variety of one-pot transformations to provide boron-substituted allylic alcohols, dienols, [alpha]-hydroxy ketones, and [alpha]-dihydroxy ketones with high diastereoselectivity. More applications of these reagents are also explored in Chapters 3 and 4.
Author: Nusrah Hussain
Publisher:
ISBN:
Category :
Languages : en
Pages : 596
Get Book Here
Book Description
The efficient stereoselective formation of C-C and C-O bonds remains a critical challenge in organic chemistry. The level difficulty of these bond formations increases dramatically when regio-, diastereo-, and chemoselectivity issues are present. In efforts to address such challenges, this thesis summarizes three successful strategies to develop highly stereoselective C-C and C-O bond formation reactions: 1) the first strategy outlines the direct metallation and subsequent chemo- and regioselective cross-coupling of benzylic sp3-hybridized C-H bonds (pKa values >34) to form C- bonds via palladium catalyzed deprotonative cross-coupling process (DCCP), 2) the second strategy outlines the application of 1,1-heterobimetallic borozinc reagents in the diastereoselective C- bond-forming reactions, and 3) the third strategy outlines the use of transition metal-catalysis in the highly chemo- and diastereoselective C-O bond formation via vanadium catalyzed directed epoxidation. Chapters 1 and 2 summarize a program that we have recently initiated in our laboratory known as deprotonative cross-coupling process (DCCP). DCCP is the reversible in situ deprotonation of weakly acidic sp3-hybridized C-H bonds under mild conditions, which are then catalytically cross-coupled with aryl electrophiles under palladium catalysis. Chapters 3 and 4 summarize the potential usefulness of 1-alkenyl-l,l-heterobimetallics in the stereoselective C-C bond formations in organic synthesis. Our group reported a practical generation of 1,1-heterobimetallics from air-stable B(pin)-substituted alkynylboronate esters and demonstrated their utility in a variety of one-pot transformations to provide boron-substituted allylic alcohols, dienols, [alpha]-hydroxy ketones, and [alpha]-dihydroxy ketones with high diastereoselectivity. More applications of these reagents are also explored in Chapters 3 and 4.
Author: Pher G. Andersson
Publisher: John Wiley & Sons
ISBN: 3527330976
Category : Science
Languages : en
Pages : 375
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Book Description
C-H, C-O, C-C, and C-Heteroatom bond forming processes by using metal-ligand approaches for the synthesis of organic compounds of biological, pharmacological and organic nanotechnological utility are the key areas addressed in this book. Authored by a European team of leaders in the field, it brings together innovative approaches for a variety of catalysis reactions and processes frequently applied in organic synthesis into a handy reference work. It covers all major types of catalysis, including homogeneous, heterogeneous, and organocatalysis, as well as mechanistic and computational studies. Special attention is paid to the improvements in efficiency and sustainability of important catalytic processes, such as selective oxidations, hydrogenation, and cross-coupling reactions, and to their utilization in industry. The result is a valuable resource for advanced researchers in both academia and industry, as well as graduate students in organic chemistry aiming for chemo-, regio- or stereoselective synthesis of organic compounds by using novel catalytic systems.
Author:
Publisher: Elsevier
ISBN: 044323700X
Category : Science
Languages : en
Pages : 338
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Book Description
Enantioselective C-C Bond Forming Reactions: From Metal Complex-, Organo-, and Bio-catalyzed Perspectives, Volume 73 in the Advances in Catalysis series, highlights new advances in the field, with this new volume presenting interesting chapters on topics such as An introduction to Chirality, Metal-catalyzed stereoselective C-C-bond forming reactions, Enantioselective C-C bond forming reactions promoted by organocatalysts based on unnatural amino acid derivatives, Enantioselective C-C bond formation in complex multicatalytic system, Gold-based multicatalytic systems for enantioselective C-C Bond forming reactions, Novel enzymatic tools for C-C bond formation through the development of new-to-nature biocatalysis, and more. - Provides the authority and expertise of leading contributors from an international board of authors - Presents the latest release in Advances in Catalysis serials - Updated release includes the latest information in the field
Author: Janine Cossy
Publisher: Walter de Gruyter GmbH & Co KG
ISBN: 3110728850
Category : Science
Languages : en
Pages : 222
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Book Description
Organozinc reagents are less reactive than Grignard reagents but they are much more chemoselective. Since the Negishi cross-coupling reaction developed by Ei-ichi Negishi, who was awarded the Nobel Price in chemistry in 2010, a number of cross-coupling reactions involving organozinc derivatives and transition metal catalysts (Pd, Ni, Fe, Co, Cu, ...) has been tuned up to form C-C bonds. This book on "Organozinc derivatives and transition metal catalysts" has been written by experts in the field and is a complement to the book entitled "Grignard reagents and transition metal catalysts" (a De Gruyter book, edited by J. Cossy). Grignard reagents or organozinc reagents, that is the question? From a given substrate, what is the best organometallic reagent and the best transition metal to form a C-C bond by using a cross-coupling reaction? The solution might be found in these two books.
Author: Michael J Krische
Publisher: Springer Science & Business Media
ISBN: 3540728791
Category : Science
Languages : en
Pages : 272
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Book Description
With contributions by numerous experts
Author: Arkadi Vigalok
Publisher: Springer
ISBN: 3642120733
Category : Science
Languages : en
Pages : 198
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Book Description
Contents: Kilian Muñiz: Transition Metal Catalyzed Electrophilic Halogenation of C-H bonds in alpha-Position to Carbonyl Groups; Arkadi Vigalok * and Ariela W Kaspi: Late Transition Metal-Mediated Formation of Carbon-Halogen Bonds; Paul Bichler and Jennifer A. Love*: Organometallic Approaches to Carbon-Sulfur Bond Formation; David S. Glueck: Recent Advances in Metal-Catalyzed C-P Bond Formation; Andrei N. Vedernikov: C-O Reductive Elimination from High Valent Pt and Pd Centers; Lukas Hintermann: Recent Developments in Metal-Catalyzed Additions of Oxygen Nucleophiles to Alkenes and Alkynes; Moris S. Eisen: Catalytic C-N, C-O and C-S bond formation promoted by organoactinide complexes.
Author: Aiwen Lei
Publisher: Springer
ISBN: 3662581043
Category : Science
Languages : en
Pages : 198
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Book Description
This book is a comprehensive text covering the research and development trends in the booming field of transition metal catalyzed oxidative cross-coupling reactions. Oxidative cross-coupling reaction is a new method to forming chemical bonds besides the traditional cross-coupling reactions. This book provides the answers to how this coupling reaction occurs and what its advantages are. The palladium, copper and iron catalyzed oxidative cross-coupling reactions as the main focuses of interest are described in detail. The oxidative cross-coupling reactions catalyzed by other metals and transition-metal-free oxidative coupling reactions are also introduced.This book provides a useful reference source for researchers and graduates in the field of transition metal catalyzed coupling reactions. It is also valuable to researchers working in pharmaceutical companies, fine organic chemical companies, and etc.
Author: Andrei K. Yudin
Publisher: John Wiley & Sons
ISBN: 3527633405
Category : Science
Languages : en
Pages : 541
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Book Description
Written by an experienced editor widely acclaimed within the scientific community, this book covers everything fromo9xygen to nitrogen functionalities. From the contents: Palladium-Catalyzed Syntheses of Five-Member Saturated Heterocyclic and of Aromatic Heterodynes Palladium-Catalysis for Oxidative 1, 2-Difunctionalization of Alkenes Rhodium-Catalyzed Amination of C-H-Bonds Carbon-Heteroatom Bond Formation by RH(I)-Catalyzed Ring-Opening Reactions Transition Metal-Catalyzed Synthesis of Lactones and of Monocyclic and Fused Five-Membered Aromatic heterocycles the Formation of Carbon-Sulfur and Carbon-Selenium bonds by Substitution and Addition reactions catalyzed by Transition Metal Complexes New Reactions of Copper Acetylides Gold Catalyzed Addition of Nitrogen, Sulfur and Oxygen Nucleophiles to C-C Multiple Bonds. The result is an indispensable source of information for the Strategic Planning of the Synthetic routes for organic, catalytic and medicinal chemists, as well as chemists in industry.
Author: Aiwen Lei
Publisher: John Wiley & Sons
ISBN: 3527681019
Category : Technology & Engineering
Languages : en
Pages : 240
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Book Description
The first handbook on this emerging field provides a comprehensive overview of transition metal-catalyzed coupling reactions in the presence of an oxidant. Following an introduction to the general concept and mechanism of this reaction class, the team of authors presents chapters on C-C cross-coupling reactions using organometallic partners, C-Heteroatom bond forming reactions via oxidative couplings, and C-H couplings via C-H activation. The text also covers such groundbreaking topics as recent achievements in the fields of C-C and C-X bond formation reactions as well as C-H activation involving oxidative couplings. With its novel and concise approach towards important building blocks in organic chemistry and its focus on synthetic applications, this handbook is of great interest to all synthetic chemists in academia and industry alike.
Author: Masahiro Murakami
Publisher: John Wiley & Sons
ISBN: 352768011X
Category : Technology & Engineering
Languages : en
Pages : 292
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Book Description
Edited by leading experts and pioneers in the field, this is the first up-to-date book on this hot topic. The authors provide synthetic chemists with different methods to activate carbon-carbon sigma bonds in organic molecules promoted by transition metal complexes. They explain the basic principles and strategies for carbon-carbon bond cleavage and highlight recently developed synthetic protocols based on this methodology. In so doing, they cover cleavage of C-C bonds in strained molecules, reactions involving elimination of carbon dioxide and ketones, reactions via retroallylation, and cleavage of C-C bonds of ketones and nitriles. The result is an excellent information source for researchers in academia and industry working in the field of synthetic organic chemistry, while equally serving as supplementary reading for advanced courses in organometallic chemistry and catalysis.
