Table 1.

Optimization Studies of the Reaction of o-(Trimethylsilyl)phenyl Triflate (1a) and N-Hydroxybenzimidoyl Chloride (2a)

entry	1a equiv	fluoride source (equiv)	solvent	temp (°C)	add. time of 2a (h)	% yieldb
1	1.2	CsF (3)	CH3CN	rt	-	46
2	1.2	TBAT (3)	CH3CN	rt	-	<5c
3	1.2	CsF (3)	THF	rt	-	<5c
4	1.2	CsF (3)	THF	65	-	<5c
5	1.2	CsF (3)	CH3CN	65	-	9
6	1.2	CsF (2.5)	CH3CN	rt	-	23
7	2.0	CsF (6)	CH3CN	rt	-	61
8	3.0	CsF (6)	CH3CN	rt	-	58
9	2.0	CsF (6)	CH3CN	rt	5.0	70
10	2.0	CsF (6)	CH3CN	rt	2.5	90
11	2.0	CsF (6)	CH3CN	rt	1.0	73

^aAll reactions were carried out on a 0.25 mmol scale.

^bIsolated yields, unless stated otherwise.

^c1H NMR spectroscopic yields.