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
Divergent copper-mediated dimerization and hydroxylation of benzamides involving C-H bond functionalization.
TL;DR: Convenient methods were developed for copper-mediated oxidative C-H activation of aminoquinoline benzamides to give either hydroxylation or dimerization compounds as the major products efficiently.
Journal ArticleDOI
Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium
TL;DR: An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed.
Journal ArticleDOI
Copper-catalyzed oxidative trimerization of indoles by using TEMPO to construct quaternary carbon centers: the synthesis of 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones
TL;DR: In this paper, a simple, convenient, and efficient synthesis of 2-(1H-indol-3-yl)-2,3′-biindolin-1-one derivatives has been developed by the oxidative trimeric reaction of indoles using the TEMPO/CuCl2 catalyst.
Journal ArticleDOI
Generating and optimizing the catalytic activity in UiO-66 for aerobic oxidation of alkenes by post-synthetic exchange Ti atoms combined with ligand substitution
Andrea Santiago-Portillo,Sergio Navalón,Mercedes Alvaro,Hermenegildo García,Hermenegildo García +4 more
TL;DR: The catalytic activity for the aerobic epoxidation of cyclooctene of UiO-66 has been introduced by post-synthetic ion exchange of Zr4+ by Ti4+ at the nodes and the performance optimized by nitro substitution in the terephthalate ligand as discussed by the authors.
Journal ArticleDOI
Synthesis of α-Substituted Primary Benzylamines through Copper-Catalyzed Cross-Dehydrogenative Coupling
TL;DR: A copper-catalyzed route to α-substituted, primary benzylamines by C-H functionalization of alkylarenes is described, which directly affords the amine hydrochloride salt.
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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