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Cobalt-catalyzed Electrooxidative C-H/N-H [4+2] Annulation With Ethylene Or Ethyne

Shan Tang, Dan Wang, Yichang Liu, Li Zeng, Aiwen Lei
Published 2018 · Biology, Medicine
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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.Catalytic methodologies that incorporate commodity chemicals ethylene and ethyne into fine chemicals are quite limited. Here, the authors show a cobalt-catalyzed electrochemical C-H/N–H [4+2] annulation of aryl/vinyl amides with ethylene or ethyne to produce N-heterocycles in absence of oxidants.
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