Optimization for O-arylation^a.

Entry	Base	Solvent	3aa (%)	4aa (%)
1	Pyridine	Toluene	5	41
2	2,6-Lutidine	Toluene	6	51
3	Pyrazine	Toluene	2	18
4	Isoquinoline	Toluene	5	40
5	Quinoline	Toluene	2	47
6	Quinoline	Dioxane	1	18
7	Quinoline	DMA	9	12
8	Quinoline	DMSO	4	4
9	Quinoline	FPh	2	20
10	Quinoline	ClPh	Trace(trace)b	79(96)b

^aReaction conditions: 1a (1 mmol), Ph₂IOTf (1.2 equiv.), base (2 equiv.), solvent (2 mL), 110 °C, 16 h.

^b130 °C.