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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Copper‐Catalyzed Regioselective C5 Sulfenylation of Imidazo[2,1‐b]thiazoles with Thiols
TL;DR: Copper-catalyzed regioselective sulfenylation of imidazo[2,1-b]thiazoles with thiols is described via intermolecular CS bond formation using O2 as an oxidant.
Journal ArticleDOI
Cu(OAc)2 Mediated Synthesis of 3-Sulfonyl Chromen-4-ones
TL;DR: The uses of various metal complexes and activating reagents are investigated for facile and efficient transformation and a plausible mechanism is proposed.
Journal ArticleDOI
Photoinduced Heterogeneous C−H Arylation by a Reusable Hybrid Copper Catalyst
Isaac Choi,Valentin Müller,Gaurav Lole,Robert Köhler,Volker Karius,Wolfgang Viöl,Christian Jooss,Lutz Ackermann +7 more
TL;DR: The versatile hybrid copper catalyst provided step‐economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides and could be reused without significant loss of catalytic efficacy.
Journal ArticleDOI
Selective Oxidative Esterification from Two Different Alcohols via Photoredox Catalysis
TL;DR: In this article, a simple method for ester synthesis from two different alcohols has been achieved under neutral conditions using O2 as the terminal oxidant, and a variety of primary alcohols, especially long chain alcohols and secondary alcohols are tolerated in this system.
Journal ArticleDOI
CuI-catalyzed oxidative cross coupling of oximes with tetrahydrofuran: a direct access to O-tetrahydrofuran-2-yl oxime ethers
TL;DR: An efficient copper(I)-catalyzed oxidative tetrahydrofuranylation of oximes has been developed in this paper, which shows good functional group tolerance and various substituted ketoximes and aldoximes coupled smoothly with THF to give the corresponding O-tetrahydron-2-yl oxime ethers in high yields.
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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