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

Xia Zhao, Aoqi Wei, Xiaoyu Lu, Kui Lu

Molecules. 2017 Aug 1;22(8):1208.

PMID: 28763049

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP311284 Tetrabutylammonium iodide Tetrabutylammonium iodide 311-28-4 Price
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