Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 11-12, Pages 1861-1869Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900905
Keywords
benzylic alcohols; chlorotrimethylsilane, direct sulfonylation; homoallylic alcohols; sodium p-toluenesulfinate
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Funding
- Council of Scientific and Industrial Research (CSIR), India
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A new protocol for the direct sulfonylation of benzylic, allylic and homoallylic alcohols with sodium arenesulfinates is described by using iron(III) chloride as a catalyst and chlorotrimethylsilane as an additive. This method requires no pre-activation of alcohols. Surprisingly in the reaction with homoallyl alcohols nucleophilic addition of sulfinate anion, occurs at the terminal double bond instead of nucleophic substitution at the alcohol.
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