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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Metal‐Free Oxidative Cross‐Coupling Reaction of Thiophene Iodonium Salts with Pyrroles
TL;DR: In this paper, the hypervalent-iodine-mediated oxidative metal-free cross-coupling reaction of thiophenes with various pyrroles was developed.
Journal ArticleDOI
Dithiolane-Directed Tandem Oxidation/1,2-Benzyl Migration of Tetramic Acids under Ambient Conditions
TL;DR: It is reported that exposure of tetramic acids in the open air (molecular oxygen) at room temperature can lead to the formation of succinimide derivatives in high to excellent yields via tandem oxidation/1,2-benzyl migration.
Journal ArticleDOI
Air promoted annulation of thiophenols with alkynes leading to benzothiophenes.
TL;DR: Air promoted intermolecular annulation of thiophenols with alkynes, leading to complex benzothiophenes, is reported, demonstrating an atom-economical reaction in the absence of any catalyst, chemical oxidant and additive.
Journal ArticleDOI
First Principles (DFT) Characterization of RhI/dppp‐Catalyzed C ? H Activation by Tandem 1,2‐Addition/1,4‐Rh Shift Reactions of Norbornene to Phenylboronic Acid
Eric Assen B. Kantchev,Eric Assen B. Kantchev,Surya R. Pangestu,Feng Zhou,Michael B. Sullivan,Haibin Su +5 more
TL;DR: DFT calculations confirm the Rh(I) /Rh(III) mechanism and suggest that carborhodation of non-strained, open-chain substrates would be disfavored relative to protonation.
Journal ArticleDOI
Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions
TL;DR: This paper describes a method for alkene oxyamination and diamination that utilizes simple carbamate and urea groups as nucleophilic heteroatom donors and uses a tandem copper–photoredox catalyst system that is operationally convenient.
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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