Journal
TETRAHEDRON LETTERS
Volume 43, Issue 47, Pages 8479-8483Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)02073-7
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A general, mild, and convenient method has been developed for the synthesis of various alkyl and aryl sulfinic acid salts and sulfonamides from the corresponding halides. Key to the success of this methodology is the design and facile synthesis of sodium 3-niethoxy-3-oxopropane-1-sulfinate (SMOPS), a reagent that serves to introduce the protected sulfinate moiety directly to the substrate, thus avoiding the use of oxidizing and other harsh reaction conditions such as organolithium or Grignard reagents. Many functional groups, as well as heterocycles, are tolerated in the sequence. (C) 2002 Published by Elsevier Science Ltd.
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