Non-reductive Desulfenylation of 3-Thioalkyl-2-oxindoles

Terrence J. Connolly; Tony Durst

doi:10.1055/s-1996-5571

Synlett 1996; 1996(7): 663-664
DOI: 10.1055/s-1996-5571

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Non-reductive Desulfenylation of 3-Thioalkyl-2-oxindoles

Terrence J. Connolly, Tony Durst^*

^*Ottawa Carleton Chemistry Institute, Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada, K1N 9B4, Fax (613) 562 5170, Bitnet tdurst@oreo.chem.uottawa.ca

Abstract

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A mild, non-reductive method for the desulfenylation of 3-thioalkyl-2-oxindoles has been developed. The reaction conditions, consisting of stirring the substrate with 1.2 equivalents of TsOH and PPh₃, are tolerant to a variety of functional groups including halogens, nitro and carbonyl groups, and isolated double bonds. Yields in all cases are 80 to >95%. Desulfinylation is also possible, although in a slightly lower yield.

Desulfenylation - non-reductive - oxindole

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