Table 1.

Reaction Optimization and Influence of Bases on Reaction Outcome^a

entry	base	temperature (°C)	additives	yield (%)b
1	LiOt-Bu	26 (rt)		80c (86)
2	NaOt-Bu	rt		44
3	KOt-Bu	rt		20
4	none	rt		0
5	LiOt-Bu	40		76
6	CS2CO3	rt		15
7	K2CO3	rt		0
8	LiOH·H2O	rt		19
9	LiOAc	rt		0
10	LiOMe	rt		41
11	Et3N	rt		19
12	pyridine	rt		0
13d	LiOt-Bu	rt	air	22
14e	LiOt-Bu	rt	light	78
15f	LiOt-Bu	rt		62
16g	LiOt-Bu	50	CH2Cl2	47
17g	LiOt-Bu	50	DCE	72

^aAll reactions were performed using 1 mL of anhydrous, degassed, nonstabilized THF, 0.14 mmol of N-chlorophthalimide, and 0.14 mmol of LiOt-Bu under an argon atmosphere, with constant stirring in the dark, and at room temperature, unless stated otherwise.

^bNMR yield obtained using dibromomethane as an internal standard.

^cIsolated yield.

^dThe reaction was performed in an open atmosphere.

^eThe reaction was performed without covering the reactor in aluminum foil to allow ambient light in the reaction flask.

^fStabilized reagent-grade THF was used without further purification and without degassing.

^gThe reaction was performed using a 1:1 ratio of THF and the additive solvent (total volume 1 mL).