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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Aerobic oxysulfonylation of alkenes using thiophenols: an efficient one-pot route to β-ketosulfones
TL;DR: A highly efficient synthetic route to β-ketosulfones via AgNO3 catalyzed oxysulfonylation of alkenes using thiophenols in the presence of air and K2S2O8 as eco-friendly oxidants is developed.
Journal ArticleDOI
Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives.
Bin Li,Huiliang Feng,Nuancheng Wang,Jianfeng Ma,Haibin Song,Shansheng Xu,Baiquan Wang,Baiquan Wang +7 more
TL;DR: The mechanism of [{RuCl(2)(p-cymene)}(2)]-catalyzed oxidative annulations of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through C-H/N-H activation was investigated in detail.
Journal ArticleDOI
A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C–H Bond Activation Followed by C–C and C–O Bond Formation
TL;DR: In this tandem catalytic synthesis of 3-aroylindoles both C-C and C-O bonds are installed at the expense of two sp(3) C-H bond cleavages.
Journal ArticleDOI
Copper-catalyzed aerobic oxidative synthesis of aryl nitriles from benzylic alcohols and aqueous ammonia
TL;DR: Copper-catalyzed direct conversion of benzylic alcohols to aryl nitriles was realized using NH3(aq.) as the nitrogen source, O2 as the oxidant and TEMPO as the co-catalyst.
Journal ArticleDOI
Structural and Reactivity Models for Copper Oxygenases: Cooperative Effects and Novel Reactivities
TL;DR: Tyrosinase is a copper-based O2-activating enzyme, whose structure and reactivity have been widely studied, and that serves as a paradigm for O2 activation at a dimetal site as discussed by the authors.
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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