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. 2018 Jun 4;3(6):5994–6005. doi: 10.1021/acsomega.8b00726

Table 1. Optimization of the Reaction Conditions for the Model Reactiona.

graphic file with name ao-2018-007268_0005.jpg

entry solvent promoter t (°C) time (h) yieldb (%)
1 CH3CN   reflux 12 nr
2 CH3CN AgOTf reflux 12 nr
3 CH3CN Cu(OTf)2 reflux 12 nr
4 CH3CN K2CO3 reflux 12 33
5 CH3CN Cs2CO3 reflux 12 62
6 1,4-dioxane Cs2CO3 reflux 12 68
7 1,4-dioxane t-BuOK reflux 12 complex
8 CH3CN DBU reflux 12 82
9 1,4-dioxane DBU reflux 12 nr
10 acetonec DBU reflux 12 90
11 EtOH DBU reflux 12 12
12 acetone DABCO reflux 12 nr
13 acetone Et3N reflux 12 nr
14 acetone DBU reflux 8 85
15 acetone DBU reflux 16 89
a

Reaction conditions: 1a (1.1 mmol), 3a (1.0 mmol), base (2.0 mmol), solvent (15 mL).

b

Isolated yield based on 3a. nr = no reaction.

c

Bold entry indicates the best condition.