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Synlett 1995; 1995(9): 984-986
DOI: 10.1055/s-1995-5137
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Bismuth(III) Halides and Sulfate as Highly Efficient Catalyst for the Sulfenylation of Carbonyl and Related Compounds1

Naoki Komatsu* , Masato Uda, Hitomi Suzuki1
  • *Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-01, Japan
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Publication Date:
31 December 2000 (online)

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BiX3 (X=Cl, Br and I) and Bi2(SO4)3 act as strong catalyst for the sulfenylation of carbonyl and related compounds. Using these catalytic systems, the following types of sulfenylation have been carried out efficiently; i) S,S-acetalization of aldehydes (turnover number up to 2300) and ketones (up to 190), ii) transacetalization of acetal to O,S- and S,S-acetals (up to 1000), and iii) conjugate addition of thiophenol to α,β-unsaturated carbonyl compound (up to 48).

bismuth - S,S-acetal - O,S-acetal - catalyst - sulfenylation