Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne

Nature Communications
Shan TangAiwen Lei

Abstract

Ethylene and ethyne are among the simplest two-carbon building blocks. However, quite limited methods can be applied to incorporate ethylene or ethyne into fine chemicals. Here we demonstrate a cobalt-catalyzed dehydrogenative C-H/N-H [4+2] annulation of aryl/vinyl amides with ethylene or ethyne by using an electrochemical reaction protocol. Significantly, this work shows an example of electrochemical recycling of cobalt catalyst in oxidative C-H functionalization reactions, avoiding the use of external chemical oxidants and co-oxidants. The electrochemical method provides a reliable and safe way for incorporating gas-phase ethylene or ethyne into fine chemicals. High reaction efficiency and good functional group tolerance are observed under divided electrolytic conditions.

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Citations

Apr 1, 2018·Angewandte Chemie·Youai QiuLutz Ackermann
Jun 19, 2018·Chemical Society Reviews·Markus D Kärkäs
Sep 14, 2018·Organic & Biomolecular Chemistry·Ramasamy Manoharan, Masilamani Jeganmohan
Jun 20, 2018·Chemistry : a European Journal·Nicolas SauermannLutz Ackermann
Sep 13, 2018·Chemistry : a European Journal·Yongyuan GaoYi Pan
Nov 1, 2018·Chemistry : a European Journal·Shou-Kun ZhangLutz Ackermann
Feb 5, 2019·Angewandte Chemie·Qixue QinNing Jiao
Mar 22, 2019·ChemSusChem·Samaresh Chandra SauLutz Ackermann
Sep 11, 2019·Chemical Communications : Chem Comm·Deepti KalsiBasker Sundararaju
Jan 9, 2020·Chemical Communications : Chem Comm·Ruhuai MeiLutz Ackermann
Dec 26, 2019·Chemistry : a European Journal·Youai QiuLutz Ackermann
Feb 18, 2020·ChemSusChem·Ruhuai MeiLutz Ackermann
Dec 15, 2018·Angewandte Chemie·Jin LiGuigen Li
Apr 10, 2020·Chemical Communications : Chem Comm·Yating ZhaoWujiong Xia
Aug 7, 2019·Chemical Communications : Chem Comm·Jing-Hao WangLi-Zhu Wu
Nov 3, 2020·Organic & Biomolecular Chemistry·Partha Pratim SenSudipta Raha Roy
Jan 21, 2021·Angewandte Chemie·Yulei WangLutz Ackermann
Apr 2, 2021·ACS Central Science·Cuiju ZhuLutz Ackermann
Apr 3, 2020·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
May 25, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ramesh C Samanta, Lutz Ackermann
Jun 15, 2021·Chemical Science·Ramesh C SamantaLutz Ackermann
Aug 11, 2021·Journal of the American Chemical Society·Fabio JuliáTobias Ritter
May 31, 2018·Journal of the American Chemical Society·Ruhuai MeiLutz Ackermann

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Methods Mentioned

BETA
column chromatography

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