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
Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis.
TL;DR: This Review is intended to highlight strategic uses of these metals to realize efficient syntheses and highlight the future potential of these reagents and catalysts in organic synthesis.
Journal ArticleDOI
Mechanistic insights into cobalt(ii/iii)-catalyzed C-H oxidation: a combined theoretical and experimental study
TL;DR: In this paper, single electron transfer (SET) and the concerted metalation-deprotonation (CMD) pathways of the CoII/CoIII-catalyzed alkoxylation of C(sp2)−H bonds have been investigated for the first time using the DFT method.
Journal ArticleDOI
Copper-catalyzed aerobic oxidative cross-dehydrogenative coupling of amine and α-carbonyl aldehyde: a practical and efficient approach to α-ketoamides with wide substrate scope.
TL;DR: A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling of amine with α-carbonyl aldehyde with wide substrate scope, CDC strategy and using air as oxidant make this transformation highly efficient and practical.
Journal ArticleDOI
Copper-Catalyzed Oxidative Carbon–Carbon and/or Carbon–Heteroatom Bond Formation with O2 or Internal Oxidants
TL;DR: The efforts over the last several years to develop copper-catalyzed C-C or C-heteroatom bond formation reactions with oxygen or internal oxidants as the oxidant are described.
Journal ArticleDOI
Ruthenium-Catalyzed Pyrrole Synthesis via Oxidative Annulation of Enamides and Alkynes
TL;DR: An efficient and regioselective ruthenium-catalyzed oxidative annulation of enamides with alkynes via the cleavage of C(sp(2))-H/N-H bonds is reported.
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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