Journal ArticleDOI
Copper-Catalyzed Aerobic Oxidative C ? H Functionalizations: Trends and Mechanistic Insights
TLDR
This work has reported several recently reported Cu-catalyzed C-H oxidation reactions that feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II), and evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism.Abstract:
The selective oxidation of C-H bonds and the use of O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is a versatile oxidant, capable of promoting a wide range of oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich organic molecules. Many of these reactions can be rendered catalytic in Cu by employing molecular oxygen as a stoichiometric oxidant to regenerate the active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed C-H oxidation reactions feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II). In some of these cases, evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism. Organometallic C-H oxidation reactions of this type represent important new opportunities for the field of Cu-catalyzed aerobic oxidations.read more
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Journal ArticleDOI
Organocatalysis in Inert C–H Bond Functionalization
Yan Qin,Lihui Zhu,Sanzhong Luo +2 more
TL;DR: This review provides a comprehensive summary of organocatalysis in inert C-H bond functionalization over the past two decades as well as those activated benzylic, allylic, and C- H bonds alpha to the heteroatom such as nitrogen and oxygen.
Journal ArticleDOI
Copper-Promoted Sulfenylation of sp2 C–H Bonds
TL;DR: Application of the auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative β-C-H bonds and benzylamine derivative γ-C -H bonds to the direct trifluoromethylsulfenylations of C-H Bonds was demonstrated.
Journal ArticleDOI
Katalytische Funktionalisierung von C(sp2)-H- und C(sp3)-H-Bindungen unter Verwendung von zweizähnigen dirigierenden Gruppen
Guy Rouquet,Naoto Chatani +1 more
TL;DR: In this paper, Daugulis et al. discuss direkte Funktionalisierung von Substraten durch Aktivierung of C-H-Bindungen als eine gute Strategie, weil so die Herstellung funktionalisiersierter Ausgangsstoffe vermieden werden kann.
Journal ArticleDOI
Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay.
TL;DR: A copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C–H bonds intobenzylic nitriles is reported, providing evidence for diffusible organic radicals and highlighting the difference between these reactions and C-H oxidations mediated by enzymes and other catalysts that operate via radical rebound pathways.
Journal ArticleDOI
Cobalt‐Catalyzed, Aminoquinoline‐Directed C(sp2)H Bond Alkenylation by Alkynes
Liene Grigorjeva,Olafs Daugulis +1 more
TL;DR: A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp(2))-H bond alkenylation by alkynes was developed that shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling.
References
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Journal ArticleDOI
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
TL;DR: This is the first comprehensive review encompassing the large body of work in this field over the past 5 years, and will focus specifically on ligand-directed C–H functionalization reactions catalyzed by palladium.
Journal ArticleDOI
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.
TL;DR: A review of palladium-catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle can be found in this paper.
Journal ArticleDOI
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds
Charles S. Yeung,Vy M. Dong +1 more
Journal ArticleDOI
Multicopper Oxidases and Oxygenases
TL;DR: Copper sites have historically been divided into three classes based on their spectroscopic features, which reflect the geometric and electronic structure of the active site: type 1 or blue copper, type 2 (T2) or normal copper, and type 3 (T3) or coupled binuclear copper centers.
Journal ArticleDOI
Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
TL;DR: This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.
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