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Synfacts 2012; 8(7): 0769
DOI: 10.1055/s-0031-1291166
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

InI3-Catalyzed Synthesis of Thioethers Using Thiosilanes

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Nishimoto Y, Okita A, Yasuda M, Baba A * Osaka University, Japan
Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes.

Org. Lett. 2012;
14: 1846-1849
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Publication History

Publication Date:
19 June 2012 (online)

 
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Key words

indium - thiosilanes - thioethers - alkyl acetates

Significance

Herein, the authors disclose an ­indium triiodide catalyzed substitution of the ­acetoxy group in various alkyl acetates using thio­silanes. This method successfully converts various primary, secondary and tertiary alkyls, as well as propargylic, allylic and benzylic systems into the appropriate thioethers with a high functional group tolerance.


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Comment

The corresponding thioethers are obtained in good to excellent yields. In the case of primary alkyl acetates and α-acetoxy carbonyl derivatives, substitution is supposed to proceed via an SN2 reaction, whereas benzylic, allylic, porpargylic and secondary or tertiary alkyl acetates are substituted by an SN1-type mechanism.


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