With the optimized conditions in hand, we next investigated the scope with respect to the nucleophiles and aryl halides (Scheme 2). We found that 11 different types of nucleophiles efficiently coupled with 3,5-dimethylbromobenzene (1) or 4-bromobenzonitrile to afford the corresponding products in high yields. The reaction conditions were compatible with primary amines bearing a wide range of functional groups, including straight chains (4 and 5), a ketal (6 and 8), hydroxyl groups (7 and 12), a vinyl group , and a carbamate ester . Notably, no C-O coupling was observed for the amino alcohol substrates under the standard conditions (7 and 12). Cyclic primary amines also coupled efficiently , as did secondary amines . Notably, reactions of secondary aliphatic amines did not require an external organic base, perhaps because they can act as both a substrate and a base. Primary aliphatic , aryl , heteroaryl (30 and 31), and secondary aliphatic amides also coupled successfully, providing N-aryl amides in 53-78% yields. In addition, sulfonamides with various substituents delivered the desired products in 43-69% yields. Pyrazole also gave corresponding C-N coupling product 46 in 63% yield. Aniline, as an important substrate, undergoes a C-N crosscoupling reaction with 4,4-dimethyl-2,2'-bipyridine (d-Mebpy) as the ligand to produce the desired diarylamine product ; however, without the ligand, the reaction hardly occurs. Isolated yields are provided. For details, see Supporting Information.