Journal
TETRAHEDRON
Volume 75, Issue 25, Pages 3479-3484Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.05.010
Keywords
NBS; beta-Keto sulfones; Sulfonylation; Oxidation; Benzyl alcohols
Categories
Funding
- IIT Madras [CHY/17-18/686 847/RFIR/GSEK]
- University Grants Commission (UGC), New Delhi
- Council of Scientific and Industrial Research (CSIR), New Delhi
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An efficient synthetic route towards the synthesis of beta-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, alpha-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility. (C) 2019 Published by Elsevier Ltd.
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