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Nickel‐catalyzed three‐component coupling reaction of terminal alkynes, dihalomethane and amines to propargylamines
Author(s) -
Lanke Satish R.,
Bhanage Bhalchandra M.
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3071
Subject(s) - chemistry , catalysis , acetonitrile , halogen , nickel , coupling reaction , combinatorial chemistry , functional group , reaction conditions , component (thermodynamics) , polymer chemistry , organic chemistry , medicinal chemistry , alkyl , polymer , physics , thermodynamics
Direct C―H and C―halogen activation is an important and practical task in C―C, C―N bond formation reactions using alkynes. Propargylic amines are synthetically versatile intermediates for the preparation of many nitrogen‐containing biologically active motifs. Herein, a 15 mol% Ni(py) 4 Cl 2 /bipyridine‐catalyzed three‐component coupling reaction of alkynes, halomethane and amines through C―H and C―halogen activation was developed for the facile synthesis of propargylic amines. Tetramethylguanidine shows excellent basicity in acetonitrile and works under mild conditions. The reaction has very good functional group tolerance to aliphatic and aromatic alkynes. Copyright © 2013 John Wiley & Sons, Ltd.