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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Acetonitrile-dependent oxyphosphorylation: A mild one-pot synthesis of β-ketophosphonates from alkenyl acids or alkenes
TL;DR: In this article, an efficient one-pot synthesis of β-ketophosphonates has been developed, via the reaction of α,β-alkenyl carboxylic acids or alkenes with H-phosphates and air oxygen, catalyzed by CuSO4·5H2O in CH3CN.
Journal ArticleDOI
Copper‐Mediated Tandem C(sp2)–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐b][1,3]thiazinones
TL;DR: An efficient copper-mediated tandem C(sp2)–H sulfenylation and annulation of arenes with 2-mercaptoimidazoles to provide polycyclic fused imidazo[2,1-b][1,3]thiazinones has been developed.
Journal ArticleDOI
Selective para‐Cyanation of Alkoxy‐ and Benzyloxy‐Substituted Benzenes with Potassium Ferricyanide Promoted by Copper(II) Nitrate and Iodine
TL;DR: In this article, a simple method was developed for selective para-cyanation of alkoxy- and benzyloxy-substituted benzenes with 0.5"equivalents of potassium ferricyanide, 0.8"equivalent of copper(II) nitrate, and 0.4" equivalent of iodine in acetonitrile.
Journal ArticleDOI
Probing CuI in homogeneous catalysis using high-energy-resolution fluorescence-detected X-ray absorption spectroscopy
TL;DR: Metal-to-ligand charge transfer excitations in Cu(I) X-ray absorption spectra are introduced as spectroscopic handles for the characterization of species in homogeneous catalytic reaction mixtures by correlation of a spectral library to calculations and to complementary spectroscopy parameters.
Journal ArticleDOI
Reactivity of a stable copper–dioxygen complex
Diana A. Iovan,Alexandra T. Wrobel,Arthur McClelland,Austin B. Scharf,Guy A. Edouard,Theodore A. Betley +5 more
TL;DR: Reactivity studies highlight the unique ability of the dioxygen adduct for both hydrogen-atom abstraction and acid/base chemistry towards phenols, demonstrating that side-on superoxide species can be reactive entities.
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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