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Synlett 1991; 1991(3): 145-146
DOI: 10.1055/s-1991-20656
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Enol Borinates in Organic Synthesis: Regioselective α-Sulphenylation and α-Selenenylation of Ketones

Ian Paterson* , Simon Osborne
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 IEW, England
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Publication Date:
07 March 2002 (online)

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Enol dibutylborinates, generated in situ from ketones by enolisation with dibutylboron triflate and diisopropylethylamine, undergo efficient reaction with phenylsulphenyl chloride to give the corresponding α-phenylthio ketones, i.e. 1 → 2 → 3. High regioselectivity can be obtained by this method, which can be extended to the synthesis of (i) other α-sulphenylated ketones, e.g. 7 → 8, (ii) γ-phenylthioenones from α,β-unsaturated ketones, e.g. 11 → 12, and (iii) α-phenylseleno ketones by using phenylselenenyl chloride, e.g. 13 → 14.

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