An alternative approach towards the syntheses of thioethers and thioesters using CsF–Celite in acetonitrile

It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride–Celite. In this manner, compounds like ethanethiol, 1-pentanethio...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2002-11, Vol.43 (46), p.8281-8283
Main Authors: Shah, Syed Tasadaque Ali, Khan, Khalid Mohammed, Martinez Heinrich, Angelica, Voelter, Wolfgang
Format: Article
Language:English
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:It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride–Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters. The coupling reactions of a number of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, with alkyl, acyl or benzoyl halides in acetonitrile using cesium fluoride–Celite are described. It has been found that the CsF–Celite combination provides an efficient, convenient and practical method for syntheses of, both, thioethers and thioesters.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02028-2