Desulfurative Chlorination of Alkyl Phenyl Sulfides

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• 作者：Daniele Canestrari ; Stefano Lancianesi ; Eider Badiola ; Chiara Strinna ; Hasim IbrahimMauro F. A. Adamo
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：19
• 期：4
• 页码：918-921
• 全文大小：417K
• ISSN：1523-7052

文摘

The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl₂) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ⁴-sulfurane intermediate is proposed.