Optimization studies^a.

Entry	Additive	Oxidant	Solvent	Yieldb (%)
1	PivOH	AgOAc	THF	48
2	PivOH	AgOAc	1,4-Dioxane	26
3	PivOH	AgOAc	DCE	Trace
4	PivOH	AgOAc	MeOH	NDc
5	PivOH	AgOAc	PhMe	41
6	PivOH	AgOAc	t-AmOH	68
7	PivOH	AgF	t-AmOH	40
8	PivOH	Ag2CO3	t-AmOH	30
9	PivOH	Ag2O	t-AmOH	15
10	Zn(OAc)2	AgOAc	t-AmOH	35
11	CsOAc	AgOAc	t-AmOH	69
12	CsOPiv	AgOAc	t-AmOH	76
13	NaOAc	AgOAc	t-AmOH	70
14	HOAc	AgOAc	t-AmOH	65
15d	PivOH	AgOAc	t-AmOH	75
16e	PivOH	AgOAc	t-AmOH	40

^aReaction conditions: 1a (0.05 mmol), 2a (0.065 mmol), [RhCp*Cl₂]₂ (5 mol%), additive (0.5 equiv.), oxidant (2.3 equiv.), and solvent (1.0 mL), at 120 °C under air for 12 h.

^bIsolated yield.

^cNot detected.

^dUnder N₂.

^eAgSbF₆ (20 mol%) was used.