Table 2. Catalytic hydroamination of alkynes with primary amines ^a .

Entry	9	10	Time (h)	11, Yield b (%)
1	9a (R = Ph)	10a (R′ = Ph)	24	11aa, 98
2	9a	10b (R′ = 4-MeOC6H4)	24	11ab, 93
3	9a	10c (R′ = 4-BrC6H4)	72	11ac, 86
4	9b (R = 4-MeOC6H4)	10a	36	11ba, 90
5	9a	10b	36	11bb, 94
6	9a	10c	72	11bc, 54
7	9c (R = 3,5-Me2C6H3)	10a	36	11ca, 91
8	9d (R = 2,4,6-Me3C6H2)	10b	72	11db, 73
9	9e (R = 2,6-iPr2C6H3)	10a	72	11ea, 46
10	9e	10b	72	11eb, 44
11	9e	10c	72	11ec, 30

^aReaction conditions: 9 (2 mmol), 10 (2 mmol) benzene (3 mL).

^bIsolated yields.