Cobalt(II)‐based Metalloradical Activation of 2‐(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation | Zendy

Roy Satyajit | Zendy; Das Sandip Kumar | Zendy; Chattopadhyay Buddhadeb | Zendy

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Cobalt(II)‐based Metalloradical Activation of 2‐(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation

Author(s) -

Roy Satyajit,

Das Sandip Kumar,

Chattopadhyay Buddhadeb

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201711209

Subject(s) - cyclopropanation , cobalt , carbene , catalysis , chemistry , reaction mechanism , combinatorial chemistry , photochemistry , organic chemistry

A new catalytic method for the denitrogenative transannulation/cyclopropanation of in‐situ‐generated 2‐(diazomethyl)pyridines is described using a cobalt‐catalyzed radical‐activation mechanism. The method takes advantage of the inherent properties of a Co III ‐carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical‐activation mechanism, which is supported by various control experiments. The synthetic benefits of the metalloradical approach are showcased with a short total synthesis of (±)‐monomorine.

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