Table 1.

Vinylogous Fluorination Optimization^a

entry	catalyst	fluoride	yield (%)b
1	AgOAc	TMAF	<5
2	AgOAc	TBAFc	<5
3	AgOAc	TBABF	<5
4	AgOAc	KHF2d	<5
5	AgOAc	Fluolead™	<5
6	AgOAc	TASF	<5
7	AgOAc	Deoxo-Fluor	44
8	AgOAc	DAST	55
9	AgOAc	Et3N-3HF	90
10	AgSbF6	Et3N-3HF	88
11	AgOTf	Et3N-3HF	90

^aVinyldiazoacetate (0.4 mmol, 1.0 equiv), silver catalyst (10 mol %), fluoride source (2.0 mmol, 5.0 equiv), under refluxing in dichloromethane.

^bIsolated yield, <5 refers to no observation of product 2 from ¹H NMR analysis prior to chromatography.

^c1.0 M in THF.

^dDry DMF as solvent at 90 °C.