Table 1.

The coupling reaction of arylamines and terminal alkynes.^a

entry	amine	alkyne	product	4 (mol %)	t (h)	yd (%)b
1	X = H	R = Me	5a	5	24	43c
2	X = Me	R = Me	5b	2	24	83
3	X = i-Pr	R = Et	5c	2	24	51
4	X = OMe	R = Me	5d	1	20	90
5	X = OMe	R = n-Bu	5e	3	24	78
6	X = OPh	R = Me	5f	2	24	92
7	X = OH	R = Me	5g	5	24	38c
8		R = Me	5h	2	20	93
9		R = Ph	5i	3	24	88
10		R = C6H4-p-OMe	5j	3	24	69
11		R = 2-SC4H3	5k	2	24	94
12	R′ = OMe	R″ = OMe	5l	1	16	90
13	R′ = Cl	R″ = Me	5m	5	24	42c
14		5n		4	24	92
15		5o		4	24	85
16		5p		4	24	41c
17		5q		2	24	81

^aReaction conditions: amine (1.5 mmol), alkyne (5–10 mmol), Ru₃(CO)₁₂/HBF₄·OEt₂ (1:3), benzene (2–5 mL), 90–100 °C.

^bIsolated yield based on amine.

^c40–50% of 6 was formed.