Synlett 2013; 24(4): 487-490
DOI: 10.1055/s-0032-1318146
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Access to Cinnamates via Direct Oxidative C–H Transformation of Allylarenes

Meng-Yang Chang*
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Fax: +886(7)3125339   Email: mychang@kmu.edu.tw
,
Shin-Ying Lin
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Fax: +886(7)3125339   Email: mychang@kmu.edu.tw
,
Chieh-Kai Chan
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Fax: +886(7)3125339   Email: mychang@kmu.edu.tw
› Author Affiliations
Further Information

Publication History

Received: 14 December 2012

Accepted after revision: 10 January 2013

Publication Date:
25 January 2013 (online)


Abstract

A highly selective combination of ruthenium complex and oxidant, which catalyzes the oxidative C–H esterification of ­allylarenes to the corresponding bis-(E)-cinnamates and (E)-cinnamates, is described. The one-pot route was carried out by olefinic migration of allylarenes with RuCl2(PPh3)3 and DDQ-mediated ­allylic oxidation of the resulting internal alkenes with various ­alcohols in good yields.