Abstract 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.
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Barluenga et al. (2004) studied this question.
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