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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Journal ArticleDOI
Cu(I)-catalyzed intramolecular oxidative C-H amination of 2-aminoacetophenones: a convenient route toward isatins.
TL;DR: 2-Aminoaryl methyl ketones undergo intramolecular oxidative C-H amination to give the corresponding substituted isatins under an oxygen atmosphere in the presence of [CuI(bpy)]2.
Journal ArticleDOI
Chemical conversion of β-O-4 lignin linkage models through Cu-catalyzed aerobic amide bond formation.
TL;DR: Methods for conversion of the lignin β-O-4 models into amide derivatives and phenols have been developed, which is achieved via chemo-selective oxidation of the secondary benzylic alcohol and subsequent Cu-catalyzed aerobic amide bond formation.
Journal ArticleDOI
Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls
Tohru Kamitanaka,Koji Morimoto,Kohei Tsuboshima,Daichi Koseki,Hitoho Takamuro,Toshifumi Dohi,Yasuyuki Kita +6 more
TL;DR: A simple and efficient synthesis of phenol biaryls by the cross-couplings of quinone monoacetals and phenols is reported, with yields ranging from 58 to 90 % under mild reaction conditions and in a highly regiospecific manner.
Journal ArticleDOI
Copper-catalyzed phosphorylation of sp2 C–H bonds
TL;DR: The phosphorylation of the ortho C-H bonds in benzamides containing an 8-aminoquinoline moiety as a bidentate directing group with H-phosphonates using copper as a catalyst under mild temperature conditions shows high functional group compatibility and selectively gives mono-substituted products.
Journal ArticleDOI
Aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation: rapid entry to 7-alkylated isoquinolinediones
Shi Tang,You-Lin Deng,Jie Li,Wen-Xin Wang,Ying-Chun Wang,Zeng-Zeng Li,Li Yuan,Shi-Lu Chen,Ruilong Sheng +8 more
TL;DR: A novel copper-catalyzed aerobic oxidative cyclization of benzamides via meta-selective C-H tert-alkylation using AIBN and analogues as radical precursors was described.
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
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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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