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
Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
Journal ArticleDOI
Catalytic Functionalization of C(sp2) ? H and C(sp3) ? H Bonds by Using Bidentate Directing Groups
Guy Rouquet,Naoto Chatani +1 more
TL;DR: It would, therefore, appear that direct functionalization of substrates by activation of C-H bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials.
Journal ArticleDOI
Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications
TL;DR: This Review comprehensively highlights recent advances in intra- and intermolecular C-H amination reactions utilizing late transition metal-based catalysts using mechanistic scaffolds and types of reactions.
Journal ArticleDOI
3d Transition Metals for C-H Activation.
Parthasarathy Gandeepan,Thomas Müller,Daniel Zell,Gianpiero Cera,Svenja Warratz,Lutz Ackermann +5 more
TL;DR: A comprehensive overview on first row transition metal catalysts for C-H activation until summer 2018 is provided.
Journal ArticleDOI
Mild metal-catalyzed C–H activation: examples and concepts
TL;DR: This review presents the current state of the art in this field and detail C-H activation transformations reported since 2011 that proceed either at or below ambient temperature, in the absence of strongly acidic or basic additives or without strong oxidants.
References
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Journal ArticleDOI
An efficient copper-catalysed aerobic oxybromination of arenes in water
Jian Wang,Wei Wang,Jing-Hua Li +2 more
TL;DR: An aerobic oxybromination of arenes catalysed by Cu(NO3)2 was achieved using HBr as a bromine source, molecular oxygen as the oxidant and water as solvent with high selectivity.
Journal ArticleDOI
Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols
TL;DR: In this article, a C 2 -symmetrical 1,2-diamine was synthesized from commercial (1 R )-(+)-camphor 1 and scrutinized as ligand in the oxidative biaryl coupling of naphthol derivatives.
Journal ArticleDOI
Synthesis of Alkyl Substituted p-Benzoquinones from the Corresponding Phenols Using Molecular Oxygen Catalyzed by Copper(II) Chloride–Amine Hydrochloride Systems
TL;DR: In this paper, 2,4,6-Trimethylphenol was effectively oxidized to trimethylp-benzoquinone with molecular oxygen in the presence of a catalytic amount of copper(II) chloride-amines in alcohol at ambient temperature.
Journal ArticleDOI
α-Functionalization of non-activated aliphatic amines: ruthenium-catalyzed alkynylations and alkylations
Irina Jovel,Saisuree Prateeptongkum,Ralf Jackstell,Nadine Vogl,Christoph Weckbecker,Matthias Beller +5 more
TL;DR: Novel catalytic alpha-functionalizations of non-activated aliphatic amines with silylated alkynes are reported in the presence of the Shvo catalyst alkylations and alkynylations proceed highly selectively to the branched amines.
Journal ArticleDOI
Aryl–O reductive elimination from reaction of well-defined aryl–CuIII species with phenolates: the importance of ligand reactivity
TL;DR: A mechanistic proposal for the enhanced reactivity and the role of EPR-detected Cu(II) species will be discussed in detail.
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