Microwave-Assisted Direct Thioesterification of Carboxylic Acids

被引：10

作者：

Chou, Yen-Lin ^{[1
]}

Jhong, Yi ^{[1
]}

Swain, Sharada Prasanna ^{[1
]}

Houg, Duen-Ren ^{[1
]}

机构：

[1] Natl Cent Univ, Dept Chem, 300 Jhong Da Rd, Taoyuan 32001, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期

关键词：

NATIVE CHEMICAL LIGATION; ORGANIC-CHEMISTRY; POLYKETIDE SYNTHASE; CATALYZED SYNTHESIS; SOFT ACIDS; THIOESTERS; THIOLS; ALDEHYDES; PROTEINS; ESTERS;

D O I：

10.1021/acs.joc.7b01705

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：10201 / 10208

页数：8

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