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
Citations
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MnBr2-Catalyzed Direct and Site-Selective Alkylation of Indoles and Benzo[h]quinoline
TL;DR: Manganese-catalyzed regioselective C-H alkylation of indoles and benzo[h]quinoline with a variety of unactivated alkyl iodides is reported.
Journal ArticleDOI
Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation.
TL;DR: The photoinduced chlorination of aromatic substrates by hydrogen chloride with 2,3-dichloro-5,6-cyano-p-benzoquinone occurs efficiently to produce the corresponding monochlorinated products selectively under visible-light irradiation.
Journal ArticleDOI
Selective Hydroperoxygenation of Olefins Realized by a Coinage Multimetallic 1-Nanometer Catalyst
TL;DR: This study newly investigated the chemical reactivity of alloy SNPs obtained by the 'atom-hybridization method' and discussed the unique quantum-sized catalysts providing generally unstable hydroperoxides from the viewpoint of miniaturization and hybridization of the materials.
Journal ArticleDOI
Direct C(sp2)−H Hydroxylation of Arenes with Palladium(II)/Oxygen Using Sulfoximines as a Recyclable Directing Group
Prasenjit Das,Joyram Guin +1 more
TL;DR: The aerobic palladium(II) catalysis presented herein offers facile entry to various substituted phenols through site‐selective C−H hydroxylation of arenes by using sulfoximines as a reusable directing group.
Journal ArticleDOI
Thiourea‐Catalyzed Cross‐Dehydrogenative Coupling of C(sp3)–H with Diethyl Phosphite
TL;DR: The efficient thiourea-catalyzed cross-dehydrogenative coupling of C(sp3)–H with diethyl phosphite by using tert-butyl peroxide as a terminal oxidant was explored and provides facile access to biologically relevant α-amino phosphonic derivatives.
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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