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Copper‐Catalyzed Three‐Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines
Author(s) -
Yu Dingyi,
Zhang Yugen
Publication year - 2011
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.201000691
Subject(s) - chemistry , alkyne , halogen , nucleophile , catalysis , amine gas treating , coupling reaction , organic chemistry , combinatorial chemistry , organic synthesis , nucleophilic substitution , halide , alkyl
The direct CH and Chalogen activation for CC bond formation is one of the most interesting reactions in organic chemistry. CC bond formation using alkynes as a carbon nucleophilic source is a very useful method in synthesis. Herein, a copper(I) chloride catalyzed three‐component coupling reaction of alkynes, dihalomethanes and amines through CH and Chalogen activation to form propargylic amines under mild conditions has been established. The reaction can be conducted in water, in neat or in common organic solvents and it was applicable to both aromatic and aliphatic alkynes with good functional groups tolerance. It represents an excellent example of multi‐component reactions (MCRs), provides an elegant method for the synthesis of propargylic amines which are frequent skeletal components and synthetically versatile key intermediates for the preparation of many nitrogen‐containing biologically active compounds. From the mechanism point of view, this chemistry offers not only a new approach to propargylic amines with new CC and CN bonds formation through CH and Chalogen activation, but also provides valuable mechanistic insight into the novel multi‐component reactions.