Optimization of the reaction conditions^a.

Entry	Catalyst	Ligand	Solvent	Yieldb
1	Pd(OAc)2	PPh3	Toluene	34
2	Pd(OAc)2	PPh3	THF	Trace
3	Pd(OAc)2	PPh3	DCE	29
4	Pd(OAc)2	PPh3	Dioxane	76
5	Pd(OAc)2	PPh3	MeCN	Trace
6	Pd(OAc)2	PPh3	DMSO	Trace
7	Pd(OPiv)2	PPh3	Dioxane	31
8	Pd(TFA)2	PPh3	Dioxane	26
9	PdCl2(MeCN)2	PPh3	Dioxane	38
11	Pd(PPh3)4		Dioxane	56
12	Pd(OAc)2	BINAP	Dioxane	30
13	Pd(OAc)2	dppb	Dioxane	26
14	Pd(OAc)2	dppp	Dioxane	28
15	Pd(OAc)2	XantPhos	Dioxane	42
16	Pd(OAc)2	SPhos	Dioxane	34
17	Pd(OAc)2	XPhos	Dioxane	24
18c	Pd(OAc)2	PPh3	Dioxane	84 (80)d
19c	None	PPh3	Dioxane	0
20c	Pd(OAc)2	None	Dioxane	56
21c,e	Pd(OAc)2	PPh3	Dioxane	0
22c,f	Pd(OAc)2	PPh3	Dioxane	41
23c,g	Pd(OAc)2	PPh3	Dioxane	24
24c,h	Pd(OAc)2	PPh3	Dioxane	31
25c,i	Pd(OAc)2	PPh3	Dioxane	61

^aReaction conditions: 1a (0.1 mmol), 2a (0.15 mmol), Pd-catalyst (0.01 mmol, 10 mol%), ligand (0.02 mmol, 20 mol%), Cs₂CO₃ (0.1 mmol, 1.0 equiv.), PivOH (0.06 mmol, 0.6 equiv.), 80 °C, Ar. A solution of 1a was added via a syringe pump within 1 h.

^bNMR yield with 1-iodo-4-methoxybenzene as an internal standard.

^c T = 110 °C.

^dIsolated yield.

^eWithout Cs₂CO₃ and PivOH.

^fCsOPiv was used as the base.

^gK₂CO₃ was used as the base.

^hNa₂CO₃ was used as the base.

ⁱ5 mol% of catalyst was used.