Desulfurative Chlorination of Alkyl Phenyl Sulfides
Daniele Canestrari, Stefano Lancianesi, Eider Badiola, Chiara Strinna, Hasim Ibrahim* and Mauro F. A. Adamo*
*Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland, Email: hasimibrahimrcsi.ie, madamorcsi.ie
D. Canestrari, S. Lancianesi, E. Badiola, C. Strinna, H. Ibrahim, M. F. A. Adamo, Org. Lett., 2017, 19, 918-921.
DOI: 10.1021/acs.orglett.7b00077 (free Supporting Information)
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The use of (dichloroiodo)benzene enables a mild and rapid nucleophilic chlorination of readily available secondary and tertiary alkyl phenyl sulfides. Enantioenriched benzylic sulfides can be converted to their corresponding inverted chlorides with high stereospecificity. The chlorination of sulfa-Michael derived sulfides provides elimination-sensitive β-chloro carbonyl and nitro compounds in good yields.
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Mechanistic Hypothesis Taking into Account the Observed Stereochemistry