Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Microwave-Assisted Direct Thioesterification of Carboxylic Acids

Microwave-Assisted Direct Thioesterification of Carboxylic Acids
Sharada Prasanna Swain, Yen-Lin Chou, Duen-Ren Hou, Yi Jhong
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01705

DOI: 10.1021/acs.joc.7b01705

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