Table 1. Suzuki-Miyaura coupling of aryl halides with phenylboronic acid under Pd-P-300 catalysis.[a] .
Entry | R | X | Yield (%)[b] |
1 | H | I | >99 (91)[c] (>99)[d] |
2 | Cl | I | 98 |
3 | 4-C(O)CH3 | I | >99 |
4 | 3-NO2 | I | 93 |
5 | 4-C(O)CH3 | Br | 98 |
6 | 2-C(O)CH3 | Br | 94 |
7 | 4-NO2 | Br | 79 |
8 | 2-NO2 | Br | >99 |
9 | 4-CN | Br | 93 (60)[c] (78)[d] |
10 | 3-CN | Br | >99 |
11 | 4-CN | Cl | 81 (9)[c] (35)[d] |
Reaction conditions: aryl halide (0.6 mmol), phenylboronic acid (0.7 mmol), TBAB (1 mmol), Na2CO3 (2 mmol), Pd-P-300 (12 mol % Pd) in EtOH:H2O (2 ml:1 ml), NMR characterisation of products available in supporting information.
Isolated yields after column chromatography with n-pentane.
Isolated yield for Palladium on Carbon 10%.
Isolated yield for palladium acetate.