Water Enables Direct Use of Allyl Alcohol for Tsuji−Trost Reaction without Activators

Hidenori Kinoshita,† Hiroshi Shinokubo,*‡§ and Koichiro Oshima*†;
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan, and Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
Org. Lett., 2004, 6 (22), pp 4085–4088
DOI: 10.1021/ol048207a
Publication Date (Web): October 5, 2004
Copyright © 2004 American Chemical Society
†

 Department of Engineering.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Department of Science.

,
§

 PRESTO, Japan Science Technology Agency (JST).

, hshino@kuchem.kyoto-u.ac.jp, ; , oshima@orgrxn.mbox.media.kyoto-u.ac.jp

Abstract

Abstract Image

An aqueous biphasic reaction system enables the direct use of allyl alcohol in the Tsuji−Trost reaction without the help of any activating reagents for allyl alcohol. The reaction conditions are neutral to basic, allowing the use of amines as the nucleophile. Theoretical calculations have elucidated the importance of hydration of the hydroxy group for the smooth generation of π-allylpalladium species.

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History

  • Published In Issue October 28, 2004
  • Received September 5, 2004

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