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. 2022 Dec 7;7(50):46174–46182. doi: 10.1021/acsomega.2c04299

Table 1. Screening Reaction Conditionsa.

graphic file with name ao2c04299_0008.jpg

entry X atm. base solvent yieldd
1 3 air K2CO3 1,4-dioxane 41%
2 10 air K2CO3 1,4-dioxane 62%
3 100 air K2CO3 1,4-dioxane 87%
4 10 air K2CO3 tert-butanol 4%
5 10 air K2CO3 MeOH 59%
6 10 air K2CO3 THF 51%
7 10 air K2CO3 EtOAc 65%
8 10 air K2CO3 DCM 14%
9 10 air TMEDA 1,4-dioxane 67%
10 10 air DBU 1,4-dioxane 19%
11 10 air KOH 1,4-dioxane 14%
12 10 air DIPEA 1,4-dioxane 12%
13 10 N2 K2CO3 1,4-dioxane NR
14 10b air K2CO3 1,4-dioxane 82%
15 10c air K2CO3 1,4-dioxane 80%
a

Unless otherwise noted, all of the reactions were run with 1a (2.1 mmol), 2a (2.5 equiv), and base (2.0 equiv) under air in 10.0 mL of solvent. Equivalents (equiv) refer to the mole ratio to aniline.

b

Content value of Cu(BF4)2/AC was 7.7 mass %.

c

Content value of Cu(BF4)2/AC was 15.4 mass %.

d

Isolated yields.