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. 2020 Jun 11;5(24):14394–14407. doi: 10.1021/acsomega.0c00934

Table 1. Optimization of the Reaction Conditionsa.

graphic file with name ao0c00934_0013.jpg

entry catalyst (mol %) base (3 equiv) solvent temp (°C) oxidant yield (%) 3a
1 I2 (20)   H2O rt air 32
2 I2 (30)   H2O rt air 38
3 I2 (40)   H2O rt air 39
4 I2 (30)   H2O 50 air 62
5 I2 (30)   H2O 60 air 65
6 I2 (30)   H2O 70 air 71
7 I2 (30)   H2O 80 air 71
8 I2 (30) K2CO3 H2O 70 air 94
9 I2 (30) NaHCO3 H2O 70 air 69
10 I2 (30) Na2CO3 H2O 70 air 74
11 I2 (30) Cs2CO3 H2O 70 air trace
12 I2 (30) TEA H2O 70 air trace
13 I2 (30) DBU H2O 70 air trace
14 I2 (30) pyridine H2O 70 air trace
15 I2 (30) K2CO3 H2O 70 N2-atm 0
16   K2CO3 H2O 70 air 0
17 TBAI K2CO3 H2O 70 air trace
18 KI K2CO3 H2O 70 air trace
a

Reaction conditions: 1a (0.5 mmol, 1 equiv), 2a (1.0 mmol, 2 equiv), catalyst (0.15 mmol, 0.3 equiv) in solvent (2.0 mL) for 6 h; H2O = water, rt = room temperature.