Table 1.

Influence of ligands and Pd sources on the Suzuki-Miyaura cross-coupling of 3-chloroindazole.^[a]

	[Pd]	Ligand	Conversion [%][b]	Yield [%][c]
1	Pd2dba3	XPhos	75	56
2	Pd2dba3	SPhos	71	52
3	Pd2dba3	RuPhos	59	40
4	Pd2dba3	Pt-Bu3	23	10
5	Pd2dba3	none	<5	0
6	Pd(OAc)2	XPhos	68	49
7	Pd(OAc)2	SPhos	65	47
8	P1	XPhos	87	69
9	P2	SPhos	97	80
10	P2	SPhos	100	90[d]

^[a]Reaction conditions: 3-chloroindazole (0.25 mmol), 5-indole boronic acid (0.50 mmol), Pd source (2 mol%), ligand (3 mol%), K₃PO₄ (0.50 mmol), dioxane (1 mL), H₂O (0.2 mL), 100 °C, 15 h.

^[b]Determined by GC.

^[c]Determined by HPLC.

^[d]2.5 mol% of P2 was used.