Premium
Thioesterifications Free of Activating Agent and Thiol: A Three‐Component Reaction of Carboxylic Acids, Thioureas, and Michael Acceptors
Author(s) -
Swain Sharada Prasanna,
Chou YenLin,
Hou DuenRen
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500426
Subject(s) - chemistry , michael reaction , catalysis , thiol , amine gas treating , organic chemistry , carboxylic acid
An amine‐catalyzed, one‐pot synthesis of thioesters directly from carboxylic acids, thioureas, and Michael acceptors is described. This process was further improved by use of 1‐[2‐(methylamino)ethyl]‐3‐phenylthiourea ( 4 ) as the catalyst. Aromatic and aliphatic carboxylic acids with functional groups are compatible with this process, and both α,β‐unsaturated esters and ketones can be the Michael acceptors for this reaction. The progress of this reaction was monitored by 1 H NMR, and a reaction mechanism is proposed.