Electrochemical Synthesis of Cyanoformamides from Trichloroacetonitrile and Secondary Amines Mediated by the B12Derivative

Mohammad Moniruzzaman, Yoshio Yano, Toshikazu Ono, Kenji Imamura, Yoshihito Shiota, Kazunari Yoshizawa, Yoshio Hisaeda, Hisashi Shimakoshi

Research output: Contribution to journalArticlepeer-review

Abstract

The B12 derivative, heptamethyl cobyrinate, -mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiated in situ generation of the reactive acyl chloride intermediate, which led to cyanoformamides in the presence of an amine. This one-pot and scalable synthetic method has been demonstrated with 41 examples up to 94% yields with 21 new compounds. The mechanism of electrolysis mediated by the B12 derivative has been proposed based on the DFT calculations.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2021

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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