Cobalt-Catalyzed Migration Isomerization of Dienes

Org Lett. 2022 Jul 1;24(25):4592-4597. doi: 10.1021/acs.orglett.2c01701. Epub 2022 Jun 21.

Abstract

A cobalt-catalyzed multipositional isomerization of conjugated dienes has been reported for the first time using an 8-oxazoline iminoquinoline ligand. This reaction is operationally simple and atom-economical using readily available starting materials with an E/Z mixture to access disubstituted 1,3-dienes with excellent yields and good E,E stereoselectivity. The mechanism via alkene insertion of cobalt hydride species and β-H elimination of a π-allyl cobalt intermediate is proposed on the basis of deuterium labeling and control experiments and density functional theory calculations.