Table 5.
Entry | ArX | R | R′ | R″ | R‴ | X | Conversion (%) |
---|---|---|---|---|---|---|---|
1 | 1a | -H | -OCH3 | -H | -H | -Br | 99 |
2 | 1b | -H | -H | -OCH3 | -H | -Br | 98 |
3 | 1c | -H | -H | -H | -OCH3 | -Br | 54 |
4 c | 1c | -H | -H | -H | -OCH3 | -Br | 38 |
5 b | 1d | -H | -CH3 | -H | -H | -Br | 72 |
6 b | 1e | -H | -CHO | -H | -H | -Br | 13 |
7 b,c | 1e | -H | -CHO | -H | -H | -Br | 80 |
8 | 1f | -H | -H | -H | -H | -Br | 93 |
9 | 1g | -H | -NH2 | -H | -H | -Br | 76 |
10 | 1h | -CN | -H | -H | -H | -Br | 99 |
11 | 1i | -H | -H | -H | -H | -Cl | 55 |
a Reaction conditions: 0.268 mmol of 1a (1 eq), TBAB (0.15 eq), 0.563 mmol (2 eq) of KOH, and 2% w/w of catalyst in 2.5 mL of water under MW irradiation (T = 100 °C, 30 min). b A 0.6 eq value of TBAB. c A 10% w/w value of catalyst.