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
Geometric control of nuclearity in copper(I)/dioxygen chemistry.
Tsukasa Abe,Yuma Morimoto,Tetsuro Tano,Kaoru Mieda,Hideki Sugimoto,Nobutaka Fujieda,Takashi Ogura,Shinobu Itoh +7 more
TL;DR: Careful inspection of the crystal structures of copper(I) and copper(II) complexes and the redox potentials has revealed important geometric effects of the supporting ligands on controlling nuclearity of the generated copper active-oxygen complexes.
Journal ArticleDOI
Co(III)‐Catalyzed [4+1] Annulation of Amides with Allenes via C−H Activation
Journal ArticleDOI
Merging visible-light photoredox and copper catalysis in catalytic aerobic oxidation of amines to nitriles
TL;DR: Visible-light-initiated homogeneous oxidative synthesis of nitriles from amines was accomplished through a combined use of photoredox and copper catalysis.
Journal ArticleDOI
A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.
Zheng Huang,Mohammad S. Askari,Kenneth Virgel N. Esguerra,Tian-Yang Dai,Ohhyeon Kwon,Xavier Ottenwaelder,Jean-Philip Lumb +6 more
TL;DR: In this paper, a bio-inspired approach to the synthesis of oxindoles, which couples the energetic requirements of dehydrogenative C-N bond formation to the reduction of molecular oxygen (O2), was reported.
Journal ArticleDOI
Practical organic solvent-free Cu(OAc)2/DMAP/TEMPO-catalyzed aldehyde and imine formation from alcohols under air atmosphere
TL;DR: In this paper, a highly efficient and practical organic solvent-free Cu(OAc)2/DMAP/TEMPO catalyst system for the selective aerobic oxidation of benzylic and allylic alcohols to aldehydes and phenones under an ambient air atmosphere was reported.
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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