A mild, convenient synthesis of sulfinic acid salts and sulfonamides from alkyl and aryl halides

✍ Scribed by Jeremy M Baskin; Zhaoyin Wang

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 266 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02073-7

✦ Synopsis

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-methoxy-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.