Nickel- and rhodium-catalyzed addition of terminal silylacetylenes to propargyl amines: catalyst-dependent complementary regioselectivity.

The cross-addition of terminal silylacetylenes to gamma-arylated propargyl amines occurs efficiently via C-H cleavage by using either a nickel or rhodium catalyst. Taking advantage of the catalyst-controlled switching of regioselectivity in the reaction, both the 2- and 3-alkynylallylamines are readily accessible from the same starting materials.