Microwave-assisted direct thioesterification of carboxylic acids

Yen Lin Chou, Yi Jhong, Sharada Prasanna Swain, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.

Original languageEnglish
Pages (from-to)10201-10208
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number19
DOIs
StatePublished - 6 Oct 2017

Fingerprint

Dive into the research topics of 'Microwave-assisted direct thioesterification of carboxylic acids'. Together they form a unique fingerprint.

Cite this