Highly efficient Ni-catalyzed C-N coupling in alkane solvents

Polar solvents are often chosen for transition metal catalyzed C-N coupling reactions. In this work, it was found that the use of alkane solvents (e.g. cyclohexane, heptane) allows for highly efficient Ni-catalyzed C-N coupling of aryl pseudohalides with different types of amines in the presence of NHC ligands. Excellent functional group tolerance was achieved. Stronger hydrogen bonding effect between amine NH moiety and polar OTs/OTf in alkane solvents might be responsible for the high activity. Meanwhile, some of the obtained products showed in vitro antiproliferative activities.