Optimization of reaction conditions for Sonogashira cross-coupling reaction of iodobenzene and phenyl acetylene^a.

Entry	Catalyst (amount in mg)	Base	Solvent	Time (h)	GC-MS (% conversion)	Isolated yield (%)
1	—	K2CO3	C2H5OH	24	—	—
2	5	K2CO3	C2H5OH	24	—	—
3	5	K2CO3	H2O	24	—	—
4	10	K2CO3	C2H5OH	24	—	—
5	10	K2CO3	H2O	24	—	—
6	10	K2CO3	C2H5OH	24	—	—b
7	10	K2CO3	H2O	24	—	—b
8	10	K2CO3	C2H5OH	24	82	76c
9	10	K2CO3	H2O	24	80	71c
10	5	Et3N	H2O	24	—	—c
11	3	Et3N	C2H5OH	5	100	97c
12	5	Et 3 N	C 2 H 5 OH	5	100	99 c
13	10	Et3N	C2H5OH	5	100	99c

^aReaction conditions: iodobenzene (1 mmol), phenyl acetylene (1 mmol), base (1 mmol/10 mL), solvent (10 mL), catalyst (Pd/Cu@GO, 0.0001176 wt% Pd and 0.0002515 wt% Cu), r.t. = 29 °C in air unless otherwise noted.

^bAt 65 °C.

^cAt 75 °C.