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. 2017 Oct 11;2(10):6598–6604. doi: 10.1021/acsomega.7b01213

Table 1. Optimization of Reaction Conditionsa.

graphic file with name ao-2017-012137_0004.jpg

entry variation from the standard condition yield of 6a/7 (%)b
1 none 80/4
2 B instead of A 25/22
3 C instead of A <1/19
4 D instead of A <1/27
5 E instead of A 27/34
6 reaction at room temperature 55/3
7 Cs2CO3 instead of K2CO3 60/20
8 NEt3 instead of K2CO3 50/40
9 DBU instead of K2CO3 44/33
10 20 mol % of K2CO3, 10 mol % of NHC 67/5
11 1 equiv of K2CO3 60/17
12 CH3CN instead of THF 10/26
13 1,4-dioxane instead of THF 53/32
14 toluene instead of THF 20/15
15 1 equiv of 4a 65/5
a

Reaction conditions: 5 (1.0 equiv, 0.35 mmol), 4a (1.5 equiv, 0.52 mmol), pre-NHC catalyst A (15 mol %), K2CO3 (50 mol%), solvent (2 mL), 4 h, under argon atmosphere.

b

Isolated yields.