Table 1.

Optimization of Reaction Conditions^a

entry	mol % 2	additive	base	conversionb	yieldb
1	5	None	NaOtBu	21%	10%
2	5	None	KOtBu	23%	9%
3	5	None	LiOtBu	54%	49%
4	5	MeCN	LiOtBu	90%	86%
5c	5	MeCN	LiOtBu	100%	91%
6	5	MeCN	NaOtBu	14%	5%
7	5	MeCN	KOtBu	4%	<4%
8d	5	MeCN	LiOtBu	79%	68%
9	2.5	MeCN	LiOtBu	58%	50%
10e	2.5	MeCN	LiOtBu	68%	60%

^aReaction conditions: 3 (0.25 mmol), 4 (0.375 mmol), base (0.375 mmol) 2 (2.5 – 5 mol %), dppf (2.5 – 5 mol %), additive (0.25 mmol), CPME (0.5 mL), 100 °C, 15 min.

^bDetermined by GC using dodecane as the internal standard.

^cReaction time was 45 min. Isolated yield was 85%, 1 mmol scale, average of two runs.

^dNo additional dppf was added.

^eReaction time was 1 h.

CPME = cyclopentyl methyl ether.