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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.