Table 5.

Versatile Ligands for the Ullmann Reaction

Entry	Bond type	Copper source	Ligand	Substrates		Conditions	Yield (%)	Ref.
				Ar-X	Nucleophile
1	C-N	CuI (10 mol%)	L21	Aryl-I, Br, Cl	Anilines/Alkyl amines/Amides/Hydrazine/N-Heterocycles	K3PO4, DMF 90–120°C	32–98	46
	C-O			Aryl-I, Br, Cl	Phenols/Alkyl alcohols	Cs2CO3, DMF 110°C	20–98
	C-P			Ary-I, Br	H-phosphonates/Hy pophosphite	Cs2CO3, toluene/DMAP, DMF 110°C	20–85
2	C-N	CuI (10 mol%)	L6	Aryl-I	Amides	Cs2CO3, 110°C DMF/dioxane	73–98	81
	C-S				Thiophenols		91–98
	C-O				Phenols	Cs2CO3, 110°C dioxane	81–87
3	C-N	CuBr (10 mol%)	L5	Aryl-I, Br	Amides/N-Heterocycles	Cs2CO3, DMSO r.t.−75°C	72–96	29
	C-O				Phenols	Cs2CO3, DMSO 60–80°C	72–97
	C-S			Aryl-I	Aromatic/Alkyl thiols		81–97
4	C-N	CuI (5 mol%)	L12	E)-Vinyl-I, Br	N-Heterocycles/Phenols	Cs2CO3, DMF 60–80°C	81–95	82
	C-O			(Z)-Vinyl-I, Br	N-Heterocycles/Phenols	Cs2CO3, DMF r.t. or 40°C	81–98
5	C-N	CuI (10 mol%)	L36	Aryl-I, Br	N-Heterocycles/Aliphatic amines	Cs2CO3, DME 80°C	62–97	83
	C-O			Aryl-I, Br	Phenols		70–98
	C-S			Aryl-I	Thiophenols		75–95