Ruthenium-Catalyzed Electrochemical Dehydrogenative Alkyne Annulation DOI Creative Commons
Fan Xu, Yanjie Li, Chong Huang

et al.

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(5), P. 3820 - 3824

Published: March 9, 2018

A ruthenium-catalyzed electrochemical dehydrogenative annulation reaction of aniline derivatives and alkynes has been developed for the synthesis indoles. Electric current is used to recycle active ruthenium-based catalyst promote H2 evolution. The electrolysis operationally convenient as it employs a simple undivided cell, proceeds efficiently in an aqueous solution, insensitive air.

Language: Английский

Electrochemical C−H/N−H Activation by Water‐Tolerant Cobalt Catalysis at Room Temperature DOI
Cong Tian, Leonardo Massignan, Tjark H. Meyer

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(9), P. 2383 - 2387

Published: Jan. 10, 2018

Electrochemistry enabled C-H/N-H functionalizations at room temperature by external oxidant-free cobalt catalysis. Thus, the sustainable electrocatalysis manifold proceeds with excellent levels of chemoselectivity and positional selectivity, ample scope, thus allowing electrochemical C-H activation under exceedingly mild reaction conditions in water.

Language: Английский

Citations

234

Electroremovable Traceless Hydrazides for Cobalt-Catalyzed Electro-Oxidative C–H/N–H Activation with Internal Alkynes DOI
Ruhuai Mei,

Nicolas Sauermann,

João C. A. Oliveira

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(25), P. 7913 - 7921

Published: May 29, 2018

Electrochemical oxidative C–H/N–H activations have been accomplished with a versatile cobalt catalyst in terms of [4 + 2] annulations internal alkynes. The electro-oxidative C–H activation manifold proved viable an undivided cell setup under exceedingly mild reaction conditions at room temperature using earth-abundant catalysts. electrochemical catalysis prevents the use transition metal oxidants catalysis, generating H2 as sole byproduct. Detailed mechanistic studies provided strong support for facile cobaltation by initially formed cobalt(III) catalyst. subsequent alkyne migratory insertion was interrogated mass spectrometry and DFT calculations, providing formation key seven-membered cobalta(III) cycle regioselective fashion. Key to success unprecedented alkynes represented N-2-pyridylhydrazides, which we developed traceless electrocleavage strategy electroreductive samarium temperature.

Language: Английский

Citations

231

Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes DOI Creative Commons
Uttam Dhawa, Cong Tian, Tomasz Wdowik

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(32), P. 13451 - 13457

Published: April 3, 2020

Abstract Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective activations realized high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain highly enantiomerically‐enriched biaryls fluorinated N−C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel BINOLs, dicarboxylic acids helicenes of value asymmetric catalysis. Mechanistic studies by experiments computation key insights into catalyst's mode action.

Language: Английский

Citations

231

Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow DOI Creative Commons
Gabriele Laudadio, Sebastian Govaerts, Ying Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(15), P. 4078 - 4082

Published: Feb. 16, 2018

A mild and selective C(sp

Language: Английский

Citations

223

Ruthenium-Catalyzed Electrochemical Dehydrogenative Alkyne Annulation DOI Creative Commons
Fan Xu, Yanjie Li, Chong Huang

et al.

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(5), P. 3820 - 3824

Published: March 9, 2018

A ruthenium-catalyzed electrochemical dehydrogenative annulation reaction of aniline derivatives and alkynes has been developed for the synthesis indoles. Electric current is used to recycle active ruthenium-based catalyst promote H2 evolution. The electrolysis operationally convenient as it employs a simple undivided cell, proceeds efficiently in an aqueous solution, insensitive air.

Language: Английский

Citations

203