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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Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles.
TL;DR: In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 Å in DMF, an efficient autoxidation reaction of 2-oxindoles with ketones under air at room temperature has been developed and may provide a green, practical, and metal-free protocol.
Journal ArticleDOI
Iron-Catalyzed Regioselective Remote C(sp2)-H Carboxylation of Naphthyl and Quinoline Amides.
TL;DR: Iron(III)-catalyzed regioselective direct remote C-H carboxylation of naphthyl and quinoline amides has been developed using CBr4 and alcohol using a coordination activation strategy and single electron transfer process.
Journal ArticleDOI
A heterogeneous copper(I)-catalyzed aerobic oxidative cross-dehydrogenative coupling of terminal alkynes with thiols leading to alkynyl sulfides
TL;DR: In this paper, a heterogeneous copper-catalyzed direct oxidative cross-dehydrogenative coupling of terminal alkynes with thiols was achieved in DMSO at 70°C in the presence of an MCM-41-supported bidentate nitrogen copper(I) complex.
Journal ArticleDOI
Highly functionalized heterogeneous dendrigraft catalysts with peripheral copper moieties for the facile synthesis of 2-substituted benzimidazoles and 2,2-disubstituted benzimidazoles
TL;DR: In this paper, the synthesis of dendrigraft amidoamine polymers with glycerol initiated polyepichlorohydrin cores has been demonstrated on a Merrifield resin support to achieve heterogenosity for catalytic applications.
Journal ArticleDOI
Synthesis of β-Halo-pyrrolidinones through a Tandem Sequence of 5-Endo Halolactamization and C–H Oxidative Functionalization
TL;DR: A tandem sequence of 5-endo halolactamization and direct C-H oxidative functionalization is described, finding that a range of β-halo-pyrrolidinones can be efficiently synthesized using this method, making it an excellent approach for constructing natural products containing pyrrolids.
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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