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. 2023 Mar 27;3(3):136–142. doi: 10.1021/acsorginorgau.3c00008

Table 2. Organocatalyzed Oxindole Synthesisa.

graphic file with name gg3c00008_0006.jpg

entry variation from the standard conditions conv.b
1 none 62%
2 1b·H+ 49%
3 1c·H+ 4%
4 2a (5 mol %); 0.7 equiv of Cs2CO3 80%
5 2b (5 mol %); 0.7 equiv of Cs2CO3 38%
6 2c (5 mol %); 0.7 equiv of Cs2CO3 16%
7 [2a•+]PF6 (5 mol %); 0.7 equiv of Cs2CO3 90%
8 [2b•+]PF6 (5 mol %); 0.7 equiv of Cs2CO3 60%
a

Standard reaction conditions: 3 (0.3 mmol), precatalyst [1a·H+]PF6 (0.03 mmol), Cs2CO3 (0.24 mmol), 1,4-dioxane (1.0 mL), Ar atmosphere, 100 °C (oil bath), 16 h.

b

Estimated from 1H NMR with 1,3,5-trimethoxybenzene (TMB) as internal standard.