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
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Journal ArticleDOI
Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand.
Yixuan Chen,Yu Gui Gu,Huan Meng,Qianzhen Shao,Zhenchuang Xu,Wenjing Bao,Yu-Cheng Gu,Xiao-Song Xue,Yan-Chao Zhao +8 more
TL;DR: The key to the success of this strategy is the identification of the 3,5-dimethyl-4-isoxazolyl (DMIX) group as a superior dummy ligand, which enables not only site-selective C-H functionalization to afford unsymmetrical iodonium salts, but also highly selective aryl transfer during the subsequent metal-free coupling reaction.
Journal ArticleDOI
Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization
TL;DR: In this article, a general, simple and efficient method for the synthesis of 2-halo arylisothiocyanates from isothianates through ortho-selective halogenation under mild reaction conditions was described.
Journal ArticleDOI
Formal total synthesis of calothrixin B and its N-benzyl analogues
TL;DR: In this article, a formal total synthesis of calothrixin B and its N-benzyl analogues has been accomplished from (2-chlorophenyl)boronic acid, 8-bromophenanthridine-7,10-dione and benzylamines.
Journal ArticleDOI
Cobalt-Catalyzed Switchable Intramolecular Thioenolization/C-H Thiolation and C(sp2)-H/C(sp3)-H Dehydrogenative Coupling.
TL;DR: The selectivity for either product is achieved by accessing unique catalytic cycles involving different valence states for cobalt, as well as through an electrophilic cobaltation(III) pathway.
Journal ArticleDOI
Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid
TL;DR: Cryptosanguinolentine (isocryptolepine) is one of the minor naturallyoccurring monomeric indoloquinoline alkaloids, isolated from the West African climbing shrub Cryptolepis sanguinola as discussed by the authors.
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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