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
Copper-Catalyzed Carbamoylation of Terminal Alkynes with Formamides via Cross-Dehydrogenative Coupling
TL;DR: KIE study indicates the cleavage of the carbamoyl C–H bond affording formamide radical is the rate-determining step.
Journal ArticleDOI
Synthesis of bis(heteroaryl) ketones by removal of benzylic CHR and CO groups.
TL;DR: A copper-catalyzed method for synthesis of diaryl ketones through removal of benzylic -CH2, -CO, and -CHR- groups from Ar-CO-CXR-Ar' has been discovered and an active Cu/O2 species is proposed to mediate the rearrangement reaction.
Journal ArticleDOI
Integration of Earth-Abundant Photosensitizers and Catalysts in Metal–Organic Frameworks Enhances Photocatalytic Aerobic Oxidation
TL;DR: In this paper, two metal-organic frameworks (MOFs) were constructed by integrating earth-abundant cuprous photosensitizers (Cu-PSs) and Fe catalysts for photocataly.
Journal ArticleDOI
Auto-tandem catalysis: synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones via copper-catalyzed aza-Michael addition–aerobic dehydrogenation–intramolecular amidation
TL;DR: A copper-catalyzed domino synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed from 1,4-enediones and 2-aminoheterocycles with air as the oxidant.
Journal ArticleDOI
Copper(II)-Catalyzed Benzylic C(sp3)–H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters
TL;DR: The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from aryLacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (C═O) bond in moderate to good yield.
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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