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Synlett 2008(14): 2204-2208  
DOI: 10.1055/s-2008-1078254
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Iodine-Catalyzed Allylic Alkylation of Thiols with Allylic Alcohols

Xiaoxiang Zhang, Weidong Rao, Philip Wai Hong Chan*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, ­Singapore 637371, Singapore
Fax: +65 63166984; e-Mail: waihong@ntu.edu.sg;
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Publication History

Received 2 July 2008
Publication Date:
13 August 2008 (online)

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Abstract

An efficient iodine-catalyzed allylic alkylation of a wide variety of aryl and alkyl thiols with allylic alcohols is reported herein. The reaction is operationally straightforward, tolerant to air and moisture, and proceeds under very mild conditions at room temperature in good to excellent yields (50-92%).

Key words - allylic alcohols - allylic thioethers - alkyl and aryl thiols - carbon-sulfur bond formation - molecular-iodine catalysis

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