Mild Isomerization of Conjugated Dienes Using Co-Mediated Hydrogen Atom Transfer

Org Lett. 2020 Jan 17;22(2):750-754. doi: 10.1021/acs.orglett.9b04594. Epub 2020 Jan 8.

Abstract

A mild and high yielding rearrangement of 1,3-disubstituted-1,3-dienes to 1,1,4-trisubstituted-1,3-dienes using a cobaloxime catalyst and a silane cocatalyst is reported. Chiral centers near the conjugated diene were not racemized. Deuterium labeling studies are consistent with a hydrogen atom transfer mechanism, and radical intermediates were found to be accessible due to the observed ring opening of a cyclopropane ring.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.