TY - JOUR
T1 - Microwave-assisted direct thioesterification of carboxylic acids
AU - Chou, Yen Lin
AU - Jhong, Yi
AU - Swain, Sharada Prasanna
AU - Hou, Duen Ren
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/10/6
Y1 - 2017/10/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85044083064&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b01705
DO - 10.1021/acs.joc.7b01705
M3 - 期刊論文
C2 - 28875699
AN - SCOPUS:85044083064
SN - 0022-3263
VL - 82
SP - 10201
EP - 10208
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -