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Acetylide Ion (C 2 2− ) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis
Author(s) -
Yu Dingyi,
Sum Yin Ngai,
Ean Amanda Chng Cheng,
Chin Mei Ping,
Zhang Yugen
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301019
Subject(s) - electrophile , nucleophile , synthon , chemistry , aldehyde , aryl , combinatorial chemistry , acetylide , amine gas treating , molecule , organic chemistry , medicinal chemistry , alkyl , catalysis
Friendly competition : A three‐component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost‐efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles.