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Synfacts 2006(9): 0960-0960  
DOI: 10.1055/s-2006-949256
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of β-Keto Sulfones

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
H. Qian, X. Huang*
Hangzhou Normal College and Zhejiang University, Hangzhou, China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

A simple method for the preparation of β-keto sulfones by polystyrene-supported benzeneselenosulfonate and tolueneselenosulfonate was developed. Thus, polystyrene-supported selenenyl bromide 1 was prepared according to the reported procedures (K. C. Nicolaou et al. Chem. Commun. 1998, 1947-1948). Resin 1 reacted with sodium toluenesulfinate or sodium benzenesulfinate in DMF to give the resin-supported areneselenosulfonate 2 with a loading of 1.33 mmol/g (S). The reaction of resin 2 with acetylenes in the presence of catalytic amounts of AIBN in benzene gave the corresponding resin 4. Treatment of resin 4 with TFA gave β-keto sulfones 5a-h (8 examples, 73-51% yield from 2).