Lewis Acid‐Promoted C−H Chalcogenation of Arenes and Heteroarenes

An efficient catalytic system employing TMS•OTf for the regioselective thiolation of electron‐rich arenes with sulfonyl hydrazides has been developed. The reaction occurs in a solvent mixture of dichloroethane and trifluoroethanol under mild conditions, with the addition of water. This method furnis...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2024-12, Vol.27 (47), p.n/a
Main Authors: Vishwakarma, Rahul, Sharma, Pragya, Kumar Hazra, Chinmoy
Format: Article
Language:English
Subjects:
Aromatic compounds
Arylsulfides
Chalcogenation
Dichloroethane
Hydrazides
Indoles
Lewis acid
Sulphonyl hydrazide
Thioarylated indole
Trimethylsilyl trifluoromethanesulfonate
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient catalytic system employing TMS•OTf for the regioselective thiolation of electron‐rich arenes with sulfonyl hydrazides has been developed. The reaction occurs in a solvent mixture of dichloroethane and trifluoroethanol under mild conditions, with the addition of water. This method furnishes a range of para‐thio‐substituted arenes and 3‐sulfenyl‐indoles in good to excellent yields, marking a significant advancement in organic synthesis. A catalytic system utilizing TMS•OTf has been developed for the purpose of selectively thiolating electron‐rich arenes and heteroarenes. Environment‐friendly sulfur surrogates are employed for chalcogenation in this one‐pot single strategy, which takes place under mild conditions and yields para‐thio‐substituted arenes and 3‐sulfenyl‐indoles in good to excellent yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400894