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 coupling of aryl formamides with alcohols for the synthesis of carbamates
TL;DR: A direct transformation of N-aryl formamides to the corresponding carbamates via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine as an oxidant.
Journal ArticleDOI
Water dispersed gold nanoparticles catalyzed aerobic oxidative cross-dehydrogenative coupling: An efficient synthesis of α-ketoamides in water
TL;DR: In this article, an effective green synthesis of α-ketoamides was developed for the first time in water via gold nanoparticles (AuNPs) catalyzed aerobic oxidative cross-dehydrogenative coupling of secondary amines with phenylglyoxals with a broad substrate scope.
Journal ArticleDOI
Asymmetric synthesis of ring-fused tetrahydroquinolines using organocatalytic enantioselective conjugate addition and cross-dehydrogenative coupling
Sung Hyuk Gwon,Sung-Gon Kim +1 more
TL;DR: In this article, enantioenriched ring-fused tetrahydroquinolines were synthesized by a facile and straightforward process involving the organocatalytic enantioselective conjugate addition reaction of malonates with o - N -tetrahedroisoquinolinyl-substituted cinnamaldehyde, followed by intramolecular cross-dehydrogenative coupling.
Journal ArticleDOI
Copper-Catalyzed Aerobic Oxidative Reaction of C60 with Aliphatic Primary Amines and CS2.
Sheng-Li Wu,Xiang Gao +1 more
TL;DR: A novel type of fullerene derivatives, [60]fullerothiazolidinethione derivatives, were obtained from the copper-catalyzed aerobic oxidative reaction of C60 with aliphatic primary amines and CS2 in 4:1 v/v DMF and o-DCB.
Journal ArticleDOI
A Metallosupramolecular Octahedron Assembled from Twelve Copper(I) Metal Ions and Six 4,4′‐(1,2‐Phenylene)bis(3,5‐dimethylpyrazol‐1‐ide) Ligands
Maciej Grzywa,Björn Bredenkötter,Dmytro Denysenko,Sebastian Spirkl,Wojciech Nitek,Dirk Volkmer +5 more
TL;DR: In this article, a novel coordination compound (Cu I 12(C16H16N4)6)· 8DMAc, (2) was prepared in solvothermal or microwave assisted reaction, which contains four metall- amacrocyclic trinuclear copper(I) pyrazolate coordination units, which occupy four (opposite) faces of an imaginary metallosupramolecular octahedron.
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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