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

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 rea...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2017-08, Vol.22 (8), p.1208
Main Authors: Zhao, Xia, Wei, Aoqi, Lu, Xiaoyu, Lu, Kui
Format: Article
Language:English
Subjects:
Anions
Cancer
Chloride
Chlorides
Drug Design
Humans
Indicators and Reagents
Indoles - chemistry
Iodides
Laboratories
Metals
Natural products
Organophosphorus Compounds - chemistry
oxindole
Potassium
Quaternary Ammonium Compounds - chemistry
Reagents
Stereoisomerism
Sulfhydryl Compounds - chemistry
Sulfinic Acids - chemistry
sulfonyl chloride
Sulfur
tetrabutylammonium iodide
thiolation
triphenylphosphine
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules22081208