Table 1.

Ligand effects on the Pd-catalyzed N-arylation of 1,2,3-triazole ^[a]

entry	ligand	GC conv. (%)	GC yield of N2- arylated product (%)	N2:N1 [b]
1	L1	100	93 (90)c	97:3
2[d]	L1	9	7	N.D. [e]
3	L2	<5	<5	N.D.
4	L3	20	16	96:4
5	L4	<5	<5	N.D.

^[a]Conditions: bromobenzene (1 mmol), 1,2,3-triazole (1.2 mmol), K₃PO₄ (2 mmol), Pd₂(dba)₃ (0.75 mol%), ligand (1.8 mol%), toluene (1 mL), 120 °C, 5 h. Pd₂(dba)₃ and ligand were premixed in toluene (0.5 mL) at 120 °C for 3 min.

^[b]N²-N¹ ratio was determined by GC.

^[c]Isolated yield.

^[d]Reaction was performed without premixing Pd₂(dba)₃ and L1.

^[e]Not determined.