Influence of diverse reaction parameters on Ullmann-type synthesis of 3m^a.

Entry	Solvent	Base	Catalyst amount (mol%)	T (°C)	Time (h)	Yieldb (%)
1	H2O	Cs2CO3	1	Reflux	24	NRc
2	EtOH	Cs2CO3	1	Reflux	10	30
3	MeCN	Cs2CO3	1	Reflux	10	48
4	THF	Cs2CO3	1	Reflux	12	26
5	Toluene	Cs2CO3	1	Reflux	10	54
6	DMF	Cs2CO3	1	110	5	93
7	DMF	K2CO3	1	110	8	79
8	DMF	Et3N	1	110	12	36
9	DMF	NaOH	1	110	10	68
10	DMF	NaOAc	1	110	12	40
11	DMF	MgO	1	110	18	Trace
12	DMF	DMAP	1	110	16	45
13	DMF	Cs2CO3	1	r.t.	24	Trace
14	DMF	Cs2CO3	1	80	8	71
15	DMF	Cs2CO3	1	100	6	83
16	DMF	Cs2CO3	1	120	5	93
17	DMF	Cs2CO3	—	110	24	NR
18	DMF	Cs2CO3	0.5	110	12	47
19	DMF	Cs2CO3	0.7	110	8	76
20	DMF	Cs2CO3	0.9	110	5	90
21	DMF	Cs2CO3	1.1	110	5	93

^aImidazole (1.0 mmol), iodobenzene (1.2 mmol), base (2.0 mmol), Fe₃O₄@SiO₂-[CuL] (X mol%), and solvent (4 mL).

^bIsolated yield.

^cNo reaction.