Organic Chemistry Portal

Abstracts

Search:

Nickel(0) Triethyl Phosphite Complex-Catalyzed Allylic Substitution with Retention of Regio- and Stereochemistry

Yasutaka Yatsumonji, Yusuke Ishida, Akira Tsubouchi and Takeshi Takeda*

*Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Email: takeda-tcc.tuat.ac.jp

Y. Yatusmonji, Y. Ishida, A. Tsubouchi, T. Takeda, Org. Lett., 2007, 9, 4603-4606.

DOI: 10.1021/ol702122d (free Supporting Information)


Abstract

A nickel(0) triethyl phosphite complex promotes the reaction of allylic acetates with thiols to produce allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeds with retention of regio- and stereochemistry.

see article for more examples



Key Words

allylic sulfides, ethers


ID: J54-Y2007-3450