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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tert-Butyl Nitrite: Organic Redox Cocatalyst for Aerobic Aldehyde-Selective Wacker–Tsuji Oxidation
TL;DR: An aldehyde-selective aerobic Wacker-Tsuji oxidation is developed using tert-butyl nitrite as a simple organic redox cocatalyst instead of copper or silver salts, resulting in a variety of aldehydes achieving good to high yields at room temperature.
Journal ArticleDOI
Understanding the Effects of Bidentate Directing Groups: A Unified Rationale for sp2 and sp3 C–H Bond Activations
TL;DR: Through DFT calculations and well-defined comparative analysis, the rationale of the reactivity promoted by bidentate DG in sp(2) and sp(3) C-H activations is unified, which is generally consistent with available experimental discoveries about the C- H activation reactivity up to date.
Journal ArticleDOI
Copper-catalyzed oxidative cross-coupling of H-phosphonates and amides to N-acylphosphoramidates.
TL;DR: A simple combination of copper(II) acetate (Cu(OAc)(2) and an appropriate base could promote oxidative cross-coupling of H-phosphonates and amides using air as a terminal oxidant to give P-N coupling products in moderate to high yields.
Journal ArticleDOI
[Cu(NHC)]-Catalyzed C−H Allylation and Alkenylation of both Electron-Deficient and Electron-Rich (Hetero)arenes with Allyl Halides
Weilong Xie,Sukbok Chang +1 more
TL;DR: Not only electron-deficient but also electron-rich (hetero)arenes undergo this double-bond migration process, thus leading to alkenylated products.
Journal ArticleDOI
Copper-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology
TL;DR: A green Cu-catalyzed N-alkylation method for various amides and amines with alcohols and deduce that the newly-proposed relay race process should be the most possible and a more rational mechanism for the reactions, especially under aerobic conditions.
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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