We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a Ni-I/Ni-II catalytic cycle.