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Samarium(II) iodide-mediated deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones: synthesis of α,β-unsaturated sulfones

✍ Scribed by Vichai Reutrakul; Suwatchai Jarussophon; Manat Pohmakotr; Yupa Chaiyasut; Saengvimon U-Thet; Patoomratana Tuchinda

Book ID: 104250648
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 112 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00224-1

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✦ Synopsis

Deoxygenative debromination of a-bromo-b-hydroxy (acetoxy) phenyl sulfones with samarium(II) iodide led to substituted a,b-unsaturated sulfones in good to excellent yields. The E-isomer is the major product. A possible mechanism via an a-sulfonyl radical pathway is proposed.

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