Electrocatalytic redox neutral [3 + 2] annulation ofN-cyclopropylanilines and alkenes

Qi Wang, Qile Wang, Yuexiang Zhang, Yasmine M. Mohamed, Carlos Pacheco, Nan Zheng, Richard N. Zare, Hao Chen

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Although synthetic organic electrochemistry (EC) has advanced significantly, net redox neutral electrosynthesis is quite rare. Two approaches have been employed to achieve this type of electrosynthesis. One relies on turnover of the product by the reactant in a chain mechanism. The other involves both oxidation on the anode and reduction on the cathode in which the radical cation or the radical anion of the product has to migrate between two electrodes. Herein, a home-built electrochemistry/mass spectrometry (EC/MS) platform was used to generate anN-cyclopropylaniline radical cation electrochemically and to monitor its reactivity toward alkenes by mass spectrometry (MS), which led to the discovery of a new redox neutral reaction of intermolecular [3 + 2] annulation ofN-cyclopropylanilines and alkenes to provide an aniline-substituted 5-membered carbocycleviadirect electrolysis (yield up to 81%). A chain mechanism, involving the regeneration of the substrate radical cation and the formation of the neutral product, is shown to be responsible for promoting such a redox neutral annulation reaction, as supported by experimental evidence of EC/MS.

Original languageEnglish (US)
Pages (from-to)969-975
Number of pages7
JournalChemical Science
Volume12
Issue number3
DOIs
StatePublished - Jan 21 2021

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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