Table 2.

Development of the Ullmann O-Arylation

Entry	Copper source	Ligand	Substrates		Conditions	Yield (%)	Ref.
			Ar-X	Nucleophile
1	CuI (10 mol%)	L15	Aryl-Br	Phenols	K3PO3, CH3CN 60°C, 12 h	60–92	44
2	CuBr (10 mol%)	L23	(Hetero)Aryl-I	Phenols	Cs2CO3, DMSO 90°C	95–97	45
			(Hetero)Aryl-Br			50–98
			(Hetero)Aryl-Cl		Cs2CO3, DMSO 120°C	19–97
3	CuI (5–10mol%)	L25	(Hetero)Aryl-I	Phenols	K3PO4, DMSO 80–90°C	68–96	49
			(Hetero)Aryl-Br
4	CuI (1 mol%)	L24	Aryl-I	Phenols	Cs2CO3, CH3CN 80°C, 24 h	32–99	50
5	CuI (5 mol%)	L11	Aryl-I, Br	Aliphatic alcohol	Cs2CO3, toluene 80°C, 12 h	59–99	51
6	Cu(OTf)2 (20 mol%)	L16	Aryl-I, Br	Phenols	Cs2CO3, dioxane 110°C	60–90	52
7	CuI (5 mol%)	L18	Aryl-I, Br	Phenols	K3PO4, DMF 110°C	15–91	53
8	CuI (10 mol%)	L25	Aryl-I, Br	3-Aminophenols	K3PO4, DMSO 80–90°C	54–91	54
		L17	Aryl-I	4-Aminophenols	K2CO3, butyronitrile 70°C	38–67
9	CuI (10 mol%)	L10 or L29	Aryl-I	Phenols	KF/CP, DMSO 110°C	63–95	55
10	C1 (1–5 mol%)		Aryl-I, Br	Phenols	K3PO4, DMF 110°C	42–92	56
				Aliphatic alcohol	K3PO4, solvent-free 110°C	70–92
11	CuI (10 mol%)	L1	Aryl-I	CsOH	DMSO/H2O, 130°C	70–95	57
		L14	Aryl-Br		1,4-dioxane/H2O, NaI, 130°C	70–90
12	Cu2O (5 mol%)	L28	Aryl-I, Br, Cl	CsOH	n-Bu4N+Br− H2O, 100°C	45–96	58