Journal ArticleDOI
Labile Cu(I) Catalyst/Spectator Cu(II) Species in Copper-Catalyzed C–C Coupling Reaction: Operando IR, in Situ XANES/EXAFS Evidence and Kinetic Investigations
Chuan He,Guanghui Zhang,Guanghui Zhang,Jie Ke,Heng Zhang,Jeffrey T. Miller,Arthur Jeremy Kropf,Aiwen Lei,Aiwen Lei +8 more
TLDR
It was found that the Cu(I) complex formed from the reaction of CuI with β-diketone nucleophile was liable under the cross-coupling conditions, which is usually considered as active catalytic species.Abstract:
Insights toward the Cu-catalyzed C–C coupling reaction were investigated through operando IR and in situ X-ray absorption near-edge structure/extended X-ray absorption fine structure. It was found that the Cu(I) complex formed from the reaction of CuI with β-diketone nucleophile was liable under the cross-coupling conditions, which is usually considered as active catalytic species. This labile Cu(I) complex could rapidly disproportionate to the spectator Cu(II) and Cu(0) species under the reaction conditions, which was an off-cycle process. In this copper-catalyzed C–C coupling reaction, β-diketone might act both as the substrate and the ligand.read more
Citations
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Metal Catalysts for Heterogeneous Catalysis: From Single Atoms to Nanoclusters and Nanoparticles.
Lichen Liu,Avelino Corma +1 more
TL;DR: This Review will compare the results obtained from different systems and try to give a picture on how different types of metal species work in different reactions and give perspectives on the future directions toward better understanding of the catalytic behavior of different metal entities in a unifying manner.
Journal ArticleDOI
Copper catalysed Ullmann type chemistry: From mechanistic aspects to modern development
TL;DR: The history and development of coupling reactions between aryl halides and various classes of nucleophiles is discussed, focusing mostly on the different mechanisms proposed through the years.
Computational Explorations of Mechanisms and Ligand-Directed Selectivities of Copper-Catalyzed Ullmann-Type Reactions
TL;DR: Computational investigations of ligand-directed selectivities in Ullmann-type coupling reactions of methanol and methylamine with iodobenzene by beta-diketone- and 1,10-phenanthroline-ligated Cu(I) complexes are reported, finding N-arylation is predicted to be favored in these cases, in agreement with experimental results.
Journal ArticleDOI
Direct observation of reduction of Cu(II) to Cu(I) by terminal alkynes.
Guanghui Zhang,Hong Yi,Guoting Zhang,Yi Deng,Ruopeng Bai,Heng Zhang,Jeffrey T. Miller,Arthur Jeremy Kropf,Emilio E. Bunel,Aiwen Lei,Aiwen Lei +10 more
TL;DR: X-ray absorption spectroscopy and in situ electron paramagnetic resonance evidence were provided for the reduction of Cu(II) to Cu(I) species by alkynes in the presence of tetramethylethylenediamine (TMEDA), in which TMEDA plays dual roles as both ligand and base.
Journal ArticleDOI
Remote C-H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling.
Jun Xu,Chao Shen,Xiaolei Zhu,Pengfei Zhang,Manjaly J. Ajitha,Kuo-Wei Huang,Zhongfu An,Xiaogang Liu +7 more
TL;DR: This work reports a novel approach to activating remote C-H bonds at the C5 position of 8-aminoquinoline through copper-catalyzed sulfonylation under mild conditions and suggests that a single-electron-transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C-S cross-coupling.
References
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Journal ArticleDOI
Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.
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Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation
Steven V. Ley,Andrew Thomas +1 more
TL;DR: In this article, the authors highlight the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids as reaction partners in both O- and N-arylation.
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Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.
TL;DR: Using R-Hydroxy Stannanes as a Model for a Methylenation Reaction and Conclusions and Future Prospects are presented.
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Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions.
Florian Monnier,Marc Taillefer +1 more
TL;DR: An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.
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Copper in cross-coupling reactions: The post-Ullmann chemistry
TL;DR: A number of methods using various copper complexes and salts to carry out cross-coupling reactions leading to the formation of C heteroatom (C N, C O, C S, C P, C Se), C C, and C metal bonds have been proposed as discussed by the authors.