Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications

Chemical Reviews, Journal Year: 2017, Volume and Issue: 117(13), P. 9247 - 9301

Published: Jan. 4, 2017

Catalytic transformation of ubiquitous C-H bonds into valuable C-N offers an efficient synthetic approach to construct N-functionalized molecules. Over the last few decades, transition metal catalysis has been repeatedly proven be a powerful tool for direct conversion cheap hydrocarbons synthetically versatile amino-containing compounds. This Review comprehensively highlights recent advances in intra- and intermolecular amination reactions utilizing late metal-based catalysts. Initial discovery, mechanistic study, additional applications were categorized on basis scaffolds types reactions. Reactivity selectivity novel systems are discussed three sections, with each being defined by proposed working mode.

Language: Английский

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Bayesian reaction optimization as a tool for chemical synthesis

Nature, Journal Year: 2021, Volume and Issue: 590(7844), P. 89 - 96

Published: Feb. 3, 2021

Language: Английский

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Photoredox-Catalyzed C–H Functionalization Reactions

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1925 - 2016

Published: Sept. 29, 2021

The fields of C–H functionalization and photoredox catalysis have garnered enormous interest utility in the past several decades. Many different scientific disciplines relied on strategies including natural product synthesis, drug discovery, radiolabeling, bioconjugation, materials, fine chemical synthesis. In this Review, we highlight use reactions. We separate review into inorganic/organometallic catalysts organic-based catalytic systems. Further subdivision by reaction class─either sp2 or sp3 functionalization─lends perspective tactical for these methods synthetic applications.

Language: Английский

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Alkyl Carbon–Carbon Bond Formation by Nickel/Photoredox Cross‐Coupling

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(19), P. 6152 - 6163

Published: Oct. 6, 2018

The union of photoredox and nickel catalysis has resulted in a renaissance radical chemistry as well the use nickel-catalyzed transformations, specifically for carbon-carbon bond formation. Collectively, these advances address longstanding challenge late-stage cross-coupling functionalized alkyl fragments. Empowered by notion that photocatalytically generated radicals readily undergo capture Ni complexes, wholly new feedstocks have been realized. Herein, we highlight recent developments several types cross-couplings are accessible exclusively through this approach.

Language: Английский

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N-Heterocyclic Carbene Complexes in C–H Activation Reactions

Chemical Reviews, Journal Year: 2020, Volume and Issue: 120(4), P. 1981 - 2048

Published: Jan. 22, 2020

In this contribution, we provide a comprehensive overview of C-H activation methods promoted by NHC-transition metal complexes, covering the literature since 2002 (the year first report on metal-NHC-catalyzed activation) through June 2019, focusing both NHC ligands and methods. This review covers reactions catalyzed group 8 to 11 NHC-metal complexes. Through discussing role in promoting challenging methods, reader is provided with an important area its crucial forging carbon-carbon carbon-heteroatom bonds directly engaging ubiquitous bonds.

Language: Английский

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Selective sp3 C–H alkylation via polarity-match-based cross-coupling

Nature, Journal Year: 2017, Volume and Issue: 547(7661), P. 79 - 83

Published: June 20, 2017

Language: Английский

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Beyond C2 and C3: Transition-Metal-Catalyzed C–H Functionalization of Indole

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(9), P. 5618 - 5627

Published: July 11, 2017

The indole scaffold will continue to play a vital part in the future of drug discovery and agrochemical development. Because this, necessity for elegant techniques enable selective C–H functionalization is vast. Early developments have led primarily C2 C3 because inherent reactivity pyrrole ring. Despite methods been developed on benzenoid moiety at C4, C5, C6, C7. This review focuses contributions made indoles other related heteroaromatics such as carbazoles.

Language: Английский

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Toolbox for Distal C–H Bond Functionalizations in Organic Molecules

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(6), P. 5682 - 5841

Published: Oct. 18, 2021

Transition-metal-catalyzed C–H activation has developed a contemporary approach to the omnipresent area of retrosynthetic disconnection. Scientific researchers have been tempted take help this methodology plan their synthetic discourses. This paradigm shift helped in development industrial units as well, making synthesis natural products and pharmaceutical drugs step-economical. In vast zone bond activation, functionalization proximal bonds gained utmost popularity. Unlike bonds, distal is more strenuous requires distinctly specialized techniques. review, we compiled various methods adopted functionalize mechanistic insights within each these procedures, scope methodology. With give complete overview expeditious progress made field organic chemistry while also highlighting its pitfalls, thus leaving open for further modifications.

Language: Английский

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Photochemical Generation of Nitrogen-Centered Amidyl, Hydrazonyl, and Imidyl Radicals: Methodology Developments and Catalytic Applications

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(8), P. 4999 - 5022

Published: June 19, 2017

During the past decade, visible light photocatalysis has become a powerful synthetic platform for promoting challenging bond constructions under mild reaction conditions. These photocatalytic systems rely on harnessing energy purposes through generation of reactive but controllable free radical species. Recent progress in area established it as an enabling catalytic strategy and selective nitrogen-centered radicals. The application activation amides, hydrazones, imides represents valuable approach facilitating formation Within span only couple years, significant been made expediting amidyl, hydrazonyl, imidyl radicals from variety precursors. This Perspective highlights recent advances light-mediated these A particular emphasis is placed unique ability accessing elusive manifolds construction diversely functionalized nitrogen-containing motifs nontraditional disconnections contemporary chemistry.

Language: Английский

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Construction of Quaternary Stereocenters by Palladium‐Catalyzed Carbopalladation‐Initiated Cascade Reactions

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(6), P. 1562 - 1573

Published: June 30, 2018

Abstract The enantioselective synthesis of molecules containing quaternary stereocenters is a field intense research interest and development. Among the known organic transformations, carbopalladation‐initiated domino transformations constitutes general method for construction compounds cyclic or spiro stereocenters. In this Minireview, recent achievements in palladium‐catalyzed Heck/C−H functionalizations developments processes are summarized.

Language: Английский

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