Pd-catalyzed allylic substitution using nucleophilic N-heterocyclic carbene as a ligand

Yoshihiro Sato; Taro Yoshino; Miwako Mori

doi:10.1021/ol026961v

Pd-catalyzed allylic substitution using nucleophilic N-heterocyclic carbene as a ligand

Org Lett. 2003 Jan 9;5(1):31-3. doi: 10.1021/ol026961v.

Authors

Yoshihiro Sato¹, Taro Yoshino, Miwako Mori

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 12509883
DOI: 10.1021/ol026961v

Abstract

A nucleophilic N-heterocyclic carbene has been successfully used in a Pd(0)-catalyzed allylic substitution for the first time. It was found that allylic substitution with a soft nucleophile using a Pd-carbene catalyst proceeds via retention of configuration, the stereochemical reaction pathway being the same as that of the reaction using a Pd-phosphine complex. [reaction--see text]