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Synlett 2012(3): 413-417  
DOI: 10.1055/s-0031-1290318
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Regioselective Catalyst- and Additive-Free Synthesis of β-Keto Sulfones from Aryl Acetylenes and Sodium Arenesulfinates

Bojja Sreedhar*, Vikas S. Rawat
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology (Council of Scientific and Industrial Research), Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: sreedharb@iict.res.in;
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Publication History

Received 18 July 2011
Publication Date:
25 January 2012 (online)

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Abstract

A facile and regioselective procedure for the preparation of β-keto sulfones has been developed through a simple reaction of aryl acetylenes and sodium arenesulfinates in nitroethane as a solvent at 50 ˚C. The procedure is catalyst- and additive-free and shows a wide range of functional-group tolerance. In this system the formation of new C-O and C-S bonds occurs in a one-pot procedure.

Key words

β-keto sulfone - aryl acetylene - sodium arene sulfinates - vinyl nitronic ester - sulfone - sulfinates salt

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