Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents.

Author(s) Zhao, X.; Wei, A.; Lu, X.; Lu, K.
Journal Molecules
Date Published 2017 Aug 01

3-Sulfanyloxindoles were synthesised by triphenylphosphine-mediated transition-metal-free thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents. The above reaction was promoted by iodide anions, which was ascribed to the in situ conversion of sulfenyl chlorides into the more reactive sulfenyl iodides. Moreover, the thiolation of 3-aryloxindoles was facilitated by bases. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions make this protocol more practical for preparing 3-sulfanyloxindoles than traditional methods.

DOI 10.3390/molecules22081208
ISSN 1420-3049
Citation Molecules. 2017;22(8).

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