Comparison of results of coupling reactions of aryl halides with phenols using metal nanoparticles.

Entry	Catalyst	Conditions	X= I/Br/Cl	Number of examples	Yield (%)		Ref.
					Range	Average
1	CuNPs	MeCN, Cs2O3, 50–60 °C, 4 h	+/+/−	10	68–95	86	24
2	CuNPs	DMF, Cs2CO3, 110 °C, 24 h	+/+/−	11	60–85	75	26
3	CuONPs	DMSO, Cs2CO3, 110 °C, 18–20 h	+/+/+	18	17–94	70	27
4	CuONPs	DMSO, KOH, 110–120 °C, 14–30 h	+/+/−	28	5–98	61	28
5	CuONPs	DMAc, KOH, r.t., 16–28 h	+/+/+	21	54–92	74	29
6	CuONPs	DMF, KF.CP, 120 °C, 18–30 h	+/+/−	17	42–87	72	30
7	Cu2ONPs	THF, Cs2CO3, 150 °C, 3 h	+/+/+	11	29–100	74	31
8	CuINPs	DMF, K2CO3, 110 °C, 2–7 h	+/+/+	5	91–98	97	33
9	CuFe2O4NPs	DMF, Cs2CO3, 135 °C, 0.5–24 h	+/+/−	17	14–99	70	34
10	CuFe2O4NPs	NMP, ligand, Cs2CO3, 135 °C, 24 h	+/+/+	24	63–99	84.5	35
11	CuNPs–G	DMSO, Cs2CO3, Bu4NBr, 100 °C, 12 h	+/+/+	24	35–98	80	39
12	Cu2ONPs–G	THF, Cs2CO3, 150 °C, 3 h	+/+/−	14	20–99	79	40
13	CuNPs–G	MeCN, Cs2CO3, 80 °C, 3–15	+/+/−	32	72–96	88	41
14	CuNPs/RGO/Fe3O4 NPs	DMSO, Cs2CO3, 120 °C, 12 h	+/+/+	19	56–98	85	42
15	MWCNTs/Met/CuClNPs	DMF, K2CO3, 80 °C, 8–20 h	+/+/−	10	55–96	84	46
16	CuO@PICP	1,4-Dioxane, K3PO4, 120–135 °C, 16 h	+/+/+	30	21–99	81	47
17	Cu@MCTP-1	DMF, Cs2CO3, 130 °C, 24 h	+/+/−	29	71–96	87	48
18	TiO2–Cu2ONPs	DMF, KOH, 150 °C, 6 h	+/+/−	2	56–90	73	50
19	CuO@Fe3O4	DMF, TBAB, Cs2CO3, 145 °C, 24 h	+/+/+	18	7–97	67	51
20	Cu@Fe2O3	DMF, Cs2CO3, 130 °C, 24 h	+/−/−	12	13–99	83.5	54
21	Cu/ascorbic acid@MNPs	H2O, KOH, r.t., 12 h	+/+/−	9	67–97	88	55
22	CuI-USY	Toluene, Cs2CO3, 120–140 °C, 24 h	+/+/−	17	36–86	72	60
23	UiO-66-NH2-Mlm/CuONPs	DMSO, KOH, 110 °C, 18–24 h	+/+/+	9	30–95	74	61
24	SiC@Cu2O	THF, Cs2CO3, 150 °C, 3 h	+/+/−	14	49–98	83	62
25	SS-PdNPs	DMF, K2CO3, 80 °C, 6–10 h	+/+/+	13	48–86	68	63
26	Pd17Se15–GO	DMSO, K2CO3, r.t., 1–3 h	+/+/+	22	59–94	80	64
27	PdCl2@SDPP	Bu4NOH aq, NaOH, 70 °C, 1.5–10 h	+/+/+	14	70–99	88	65
28	Fe3O4@SiO2@PPh2@Pd0	H2O, NaOH, 80 °C, 1.5–15 h	+/+/+	11	60–93	80	66
29	Pd@ZnFe2O4	DMSO, K3PO4, 110 °C, 3.5–5 h	+/+/+	11	81–92	87	67
30	AT-CP PdNPs	H2O, K2CO3, 60 °C, 1–14 h	+/+/+	17	60–98	84.5	69
31	Pd/ZnONPs	DMF, K2CO3, 120 °C, 3–20 h	+/+/+	21	70–98	91	70
32	Ni–Al2O3	H2O, SDS, K2CO3, 100 °C, 8–12	+/+/+	40	69–89	78	71
33	NiFe2O4NPs	Dioxane, Cs2CO3, reflux, 10 h	+/+/+	5	88–95	90	72
34	CoFe2O4NPs	DMF, K2CO3, 80 °C, 1–7.5 h	+/+/+	25	81–96	88	73
35	pFe3O4@mPAMI	DMF, K2CO3, 110 °C, 12 h	−/−/+	25	55–99	84	74
36	Fe3O4NPs	Solvent-free, K2CO3, 130 °C, 48 h	+/+/+	5	43–98	68	75
37	CeO2NPs	DMF, KOH, 110 °C, 45–360 min	+/−/−	7	72–98	84.5	76
38	Au–CeO2NPs	DMSO, KOH, 110 °C, 2–24 h	−/+/+	16	3–99	65	77