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

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...

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Veröffentlicht in:Organic letters 2004-10, Vol.6 (22), p.4085-4088
Hauptverfasser: Kinoshita, Hidenori, Shinokubo, Hiroshi, Oshima, Koichiro
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048207a