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Potassium tert ‐Butoxide‐Mediated Amine Acyl Exchange Reaction of N,N ‐Disubstituted Formamides with Aromatic Carbonyl Derivatives via Sequential CN Bond Cleavage/Formation: an Approach to Aromatic Amides
Author(s) -
Zhang MingZhong,
Guo QingHu,
Sheng WenBing,
Guo CanCheng
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.201500551
Subject(s) - chemistry , formamides , reagent , bond cleavage , amine gas treating , aromatic amine , cleavage (geology) , electrophilic aromatic substitution , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
A novel potassium tert ‐butoxide‐mediated amine acyl exchange of N,N ‐disubstituted formamides with aromatic carbonyl derivatives in a sequential CN bond cleavage/formation process leading to aromatic amides is described. This methodology tolerates a wide range of aromatic carbonyl compounds, including aromatic aldehydes, acyl chlorides, unactivated esters, and acid anhydrides. The usage of inexpensive and readily available reagents, broad substrate scope, and the simple, mild (50 °C) and transition metal‐free conditions make this protocol very practical. In addition, a plausible reaction mechanism is proposed on the basis of experimental observations.