Table 3. Investigation of the Scope of Substituted Phenylboronic Acids and Aniline Derivativesa.
| entry | Ar1 | Ar2 | Pd. | yield (%)b |
|---|---|---|---|---|
| 1 | phenyl (1a) | phenyl (2a) | 3a | 94 |
| 2 | phenyl (1a) | 2-Me-C6H4 (2b) | 3b | 93 |
| 3 | phenyl (1a) | 2-Et-C6H4 (2c) | 3c | 79 |
| 4 | phenyl (1a) | 2,6-di-Me-C6H4 (2d) | 3d | 52 |
| 5 | phenyl (1a) | 3,5-di-Me-C6H4 (2e) | 3e | 72 |
| 6 | phenyl (1a) | 3-Me-C6H4 (2f) | 3f | 82 |
| 7 | phenyl (1a) | 4-Me-C6H4 (2g) | 3g | 96 |
| 8 | phenyl (1a) | 2-F-C6H4 (2h) | 3h | 24 |
| 9 | phenyl (1a) | 2-Br-C6H4 (2i) | 3i | 43 |
| 10 | phenyl (1a) | 4-F-C6H4 (2j) | 3j | 85 |
| 11 | phenyl (1a) | 4-Cl-C6H4 (2k) | 3k | 76 |
| 12 | phenyl (1a) | 3-NO2-C6H4 (2l) | 3l | 80 |
| 13 | phenyl (1a) | 3-MF-C6H4 (2m) | 3m | 94 |
| 14 | 4-NO2-C6H4 (1n) | phenyl (2a) | 3n | 74 |
| 15 | 4-Br-C6H4 (1o) | phenyl (2a) | 3o | 85 |
| 16 | 4-tert-butyl-C6H4 (1p) | phenyl (2a) | 3p | 86 |
| 17 | 4-CF3-C6H4 (1q) | phenyl (2a) | 3q | 59 |
| 18 | 3-Br-4-Cl-C6H4 (1r) | phenyl (2a) | 3r | 68 |
| 19 | 4-Me-C6H4 (1g) | phenyl (2a) | 3g | 86 |
| 20 | 4-Cl-C6H4 (1k) | phenyl (2a) | 3k | 80 |
| 21 | 2-F-C6H4 (1h) | phenyl (2a) | 3h | 62 |
| 22 | 3-NO2-C6H4 (1l) | phenyl (2a) | 3l | 83 |
| 23 | 4-piperidin-C6H4(1s) | phenyl (2a) | 3s | 75 |
a
Unless otherwise noted, all of the reactions were run with 1 (1.0 mmol), 2 (2.5 mmol), 10 mol % Cu(BF4)2/AC in 2.0 mL of MeOH. The reaction was performed using DTBP (2.0 mmol), open flask.
b
Isolated yields.