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Molecules 2017, 22(8), 1208; doi:10.3390/molecules22081208

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

1
College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key laboratory of Inorganic-organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin 300387, China
2
College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, China
*
Author to whom correspondence should be addressed.
Received: 11 July 2017 / Revised: 26 July 2017 / Accepted: 28 July 2017 / Published: 1 August 2017
(This article belongs to the Collection Heterocyclic Compounds)
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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. View Full-Text
Keywords: thiolation; oxindole; sulfonyl chloride; tetrabutylammonium iodide; triphenylphosphine thiolation; oxindole; sulfonyl chloride; tetrabutylammonium iodide; triphenylphosphine
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Zhao, X.; Wei, A.; Lu, X.; Lu, K. Tetrabutylammonium Iodide–Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents. Molecules 2017, 22, 1208.

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