Sonogashira cross-coupling reaction of various aryl halides and alkynes catalyzed by Pd/Cu@GO^a.

Entry	R1	R2	X	Product	Time (h)	GC-MS (% conversion)	Isolated yield (%)
1	H	C6H5	I		5	100	99
2	3-Methyl	C6H5	I		5	92	89
3	4-Methyl	C6H5	I		5	83	78
4	3-Nitro	C6H5	I		3	100	99
5	H	C4H9	Br		5	100	99
6	4-Methyl	C4H9	Br		5	88	84
7	4-Methoxy	C4H9	Br		5	60	53
8	4-Amino	C4H9	Br		5	96	93
9	3-Nitro	C4H9	I		5	48	45
10	H	4-MeC6H4	I		5	83	79
11	3-Methyl	4-MeC6H4	I		5	81	76
12	4-Methyl	4-MeC6H4	I		5	75	72
13	H	4-MeOC6H4	I		5	76	71
14	3-Methyl	4-MeOC6H4	I		5	63	57
15	4-Methyl	4-MeOC6H4	I		5	72	68
16	3-Nitro	4-MeOC6H4	I		5	97	91
17	H	3-NH2C6H4	I		5	63	57
18	3-Methyl	3-NH2C6H4	I		5	61	54
19	4-Methyl	3-NH2C6H4	I		5	60	53
20	3-Nitro	3-NH2C6H4	I		5	73	65

^aReaction conditions: aryl halide (1 mmol), alkyne (1 mmol), base (Et₃N, 10 mL), solvent (ethanol, 10 mL), catalyst (Pd/Cu@GO, 0.0001176 wt% Pd and 0.0002515 wt% Cu), temperature = 75 °C.