Methods for C-C and C-N Bond Formation Via Metallaphotoredox Catalysis PDF Download
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Author: Robert Wesley Pipal
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
In the field of synthetic organic chemistry, photocatalysis has emerged as a powerful visible light-driven platform for enabling the synthesis of complex molecular scaffolds. These molecules have a wide variety of important applications, spanning pharmaceuticals, agrochemicals, fragrances, and polymers. Through the merger of photoredox and transition metal catalysis, our group has shown over the last decade that numerous attractive bond disconnections can be accessed via photocatalytic generation of alkyl radicals and activated transition metal catalysts. Moreover, due to the facile nature of visible-light activation and its unique reactivity, metallaphotoredox catalysis has witnessed broad utility in radiochemical and biological applications, among others.Described herein are methods and applications of this metallaphotoredox platform. The second chapter of this thesis details a collaboration with Merck and the University of Pennsylvania for the development of a metallaphotoredox-catalyzed radiolabeling strategy. This unified and general approach allows for the installation of (radio)isotope-bearing methyl groups for applications in PET radioligand discovery. In the third chapter, a dual copper photoredox-catalyzed deoxygenative amination strategy is disclosed, effectively harnessing native and abundant alcohols as diverse alkylating reagents for C(sp3)-N bond formation. Chapter four outlines the ongoing collaboration with Janssen, delineating the late-stage peptide functionalization of alcohol-containing amino acid residues via deoxygenative C-C bond formation. Lastly, following a serendipitous discovery from the study detailed in chapter four, a mild and weakly basic dual nickel photoredox-catalyzed arylation of N-heterocycles was examined and is described in chapter five.
Author: Robert Wesley Pipal
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
In the field of synthetic organic chemistry, photocatalysis has emerged as a powerful visible light-driven platform for enabling the synthesis of complex molecular scaffolds. These molecules have a wide variety of important applications, spanning pharmaceuticals, agrochemicals, fragrances, and polymers. Through the merger of photoredox and transition metal catalysis, our group has shown over the last decade that numerous attractive bond disconnections can be accessed via photocatalytic generation of alkyl radicals and activated transition metal catalysts. Moreover, due to the facile nature of visible-light activation and its unique reactivity, metallaphotoredox catalysis has witnessed broad utility in radiochemical and biological applications, among others.Described herein are methods and applications of this metallaphotoredox platform. The second chapter of this thesis details a collaboration with Merck and the University of Pennsylvania for the development of a metallaphotoredox-catalyzed radiolabeling strategy. This unified and general approach allows for the installation of (radio)isotope-bearing methyl groups for applications in PET radioligand discovery. In the third chapter, a dual copper photoredox-catalyzed deoxygenative amination strategy is disclosed, effectively harnessing native and abundant alcohols as diverse alkylating reagents for C(sp3)-N bond formation. Chapter four outlines the ongoing collaboration with Janssen, delineating the late-stage peptide functionalization of alcohol-containing amino acid residues via deoxygenative C-C bond formation. Lastly, following a serendipitous discovery from the study detailed in chapter four, a mild and weakly basic dual nickel photoredox-catalyzed arylation of N-heterocycles was examined and is described in chapter five.
Author: Matthew West
Publisher:
ISBN:
Category : Catalysis
Languages : en
Pages : 0
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Book Description
Author: Zahra Taherinia
Publisher: Royal Society of Chemistry
ISBN: 1837671796
Category : Science
Languages : en
Pages : 334
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Book Description
Author: Marc Taillefer
Publisher: Springer
ISBN: 3642405460
Category : Science
Languages : en
Pages : 233
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Book Description
Palladium-Catalyzed sp2C–N Bond Forming Reactions: Recent Developments and Applications. Metal-catalyzed C(sp2)-N bond formation.- Recent Developments in Recyclable Copper Catalyst Systems for C−N Bond Forming Cross-Coupling Reactions Using Aryl Halides and Arylboronic Acids. Assembly of N-containing heterocycles via Pd and Cu-catalyzed C-N bond formation reactions. Copper-Catalyzed C(aryl)-N Bond Formation.
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:
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: Corey R.J. Stephenson
Publisher: John Wiley & Sons
ISBN: 3527335609
Category : Science
Languages : en
Pages : 454
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Book Description
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.
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: Zahra Taherinia
Publisher: Royal Society of Chemistry
ISBN: 1837672636
Category : Science
Languages : en
Pages : 388
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Book Description
Organic compounds containing amino groups are one of the most important classes of chemicals in both academia and industry. This class of materials is a very important structural motif in organic synthesis due to its widespread applications in natural products, agrochemicals, pharmaceuticals, and advanced materials. This book is a concise overview of modern approaches to N-alkylation and N-arylation of primary, secondary and tertiary amines using alkylating and arylating reagents with amino sources found in both basic and applied chemical research. The work also discusses key examples of amine synthesis from a sustainable perspective, using deep eutectic solvents and the application of amines in different areas. It is an ideal reference for advanced and postgraduate students as well as academic and industrial chemists working in organic, natural product, catalytic, medicinal, and polymer chemistry.
Author: Stephen David Ramgren
Publisher:
ISBN:
Category :
Languages : en
Pages : 511
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Book Description
This dissertation describes the study of metal-catalyzed cross-coupling reactions to construct carbon-carbon and carbon-heteroatom bonds. The key feature of much of this work is the use of inexpensive Ni and Fe catalysts to enable the coupling of unconventional electrophilic substrates, specifically aryl O-sulfamates and O-carbamates. The ability to use O-sulfamates and O-carbamates in catalytic processes is notable, as these substrates are readily derived from phenols and can be used for directed arene functionalization. Chapter one provides a summary of the efforts towards using alcohol-based solvents for the Suzuki-Miyaura cross-coupling reaction. Emphasis is placed on the cross-coupling of heterocycles, which are commonly encountered in natural product synthesis and in the pharmaceutical sector. Chapters two, three, and four describe carbon-nitrogen bond forming reactions. Chapter two pertains to the nickel-catalyzed amination of sulfamates, which culminated in the synthesis of the antibacterial drug, linezolid. Chapter three covers the amination of aryl O-carbamates and their use in sequential functionalization/site-selective cross-couplings. Chapter four describes a more user-friendly variant of the amination reaction, which relies on a bench-stable Ni(II) precatalyst, rather than a more commonly used Ni(0) precatalyst. Chapters five, six, and seven focus on carbon-carbon bond formation via Fe-, Ni- and Pd-mediated processes. Chapter five pertains to iron-catalyzed couplings of sulfamates and carbamates to generate sp2-sp3 carbon-carbon bonds. This method can be used to assemble sterically-congested frameworks. Chapter six describes the nickel-catalyzed Suzuki-Miyaura reactions of halides and phenol derivatives in `green' solvents, which was applied to the preparative scale assembly of bis(heterocycles) using low nickel catalyst loadings. Chapter seven pertains to the acetylation of arenes using palladium catalysis, which provides a simple and efficient means for the construction of a variety of aryl methyl ketones.
