Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach.

Author(s) Matt, C.; Kölblin, F.; Streuff, J.
Journal Org Lett
Date Published 2019 Aug 12
Abstract

A zirconium catalyzed reductive cleavage of C and C carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization of the catalyst further enables the cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.

DOI 10.1021/acs.orglett.9b02572
ISSN 1523-7052
Citation Matt C, Kölblin F, Streuff J. Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach. Org Lett. 2019.