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
Practical Methods for the Synthesis of Trifluoromethylated Alkynes: Oxidative Trifluoromethylation of Copper Acetylides and Alkynes
Cédric Tresse,Céline Guissart,Stéphane Schweizer,Yassine Bouhoute,Anne-Caroline Chany,Mary-Lorène Goddard,Nicolas Blanchard,Gwilherm Evano +7 more
TL;DR: In this paper, a mix-and-stir process was proposed for the synthesis of trifluoromethylated alkynes from readily available and bench-stable copper acetylides.
Journal ArticleDOI
Copper-Catalyzed 8-Aminoquinoline Assisted Aryl Chalcogenation of Ferroceneamide with Aryl Disulfides, Diselenides, and Ditellurides
TL;DR: It seems that the presence of a rigid chelating directing ligand is crucial for the aryl chalcogenation reaction of C-H bond under copper catalysis as the nonrigid bidentate directing ligands were unsuccessful for the transformation.
Journal ArticleDOI
Visible-light-promoted aerobic oxidative cyclization to access 1,3,4-oxadiazoles from aldehydes and acylhydrazides
TL;DR: In this article, a symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles were obtained from aldehydes and acylhydrazides using visible light irradiation under an air atmosphere in the presence of eosin Y as an organophotoredox catalyst.
Journal ArticleDOI
Expedient cobalt(II)-catalyzed site-selective C7-arylation of indolines with arylboronic acids
TL;DR: Cobalt(ii)-catalyzed pyrimidyl directing group-assisted C7 arylation of indolines with arylboronic acids has been developed using Mn(OAc)2·4H2O as an oxidant.
Journal ArticleDOI
Copper-/Cobalt-Catalyzed Highly Selective Radical Dioxygenation of Alkenes.
Qingquan Lu,Zhiliang Liu,Yi Luo,Guanghui Zhang,Zhiyuan Huang,Huamin Wang,Chao Liu,Chao Liu,Jeffrey T. Miller,Jeffrey T. Miller,Aiwen Lei,Aiwen Lei,Aiwen Lei +12 more
TL;DR: A highly selective radical dioxygenation of alkenes using hydroxamic acid and O2 was developed, and copper/cobalt was used as the catalyst without assistance of any additional ligands or bases.
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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