Premium
Palladium‐Catalyzed Amination of 1‐Bromo‐ and 1‐Chloro‐1,3‐butadienes: A General Method for the Synthesis of 1‐Amino‐1,3‐butadienes
Author(s) -
Barluenga José,
Aznar Fernando,
Moriel Patricia,
Valdés Carlos
Publication year - 2004
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.200404201
Subject(s) - chemistry , amination , palladium , catalysis , ligand (biochemistry) , combinatorial chemistry , organic chemistry , reaction conditions , amine gas treating , coupling reaction , metal , biochemistry , receptor
1‐Amino‐1,3‐butadienes, interesting substrates for [4+2] cycloadditions, are prepared by Pd‐catalyzed cross‐coupling of secondary amines with readily available 1‐halodienes. The optimized catalytic system employs Pd 2 (dba) 3 as metal source and XPHOS as supporting ligand. The reaction proceeds in very high yields with 1‐bromo‐1,3‐butadienes, and also with the less reactive 1‐chloro‐1,3‐butadienes. Moreover, the range of amines that can be incorporated includes aromatic amines, and cyclic and acyclic aliphatic amines.