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. 2014 Jan 29;9(1):e87192. doi: 10.1371/journal.pone.0087192

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]
[a]

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.

[b]

Isolated yields after column chromatography with n-pentane.

[c]

Isolated yield for Palladium on Carbon 10%.

[d]

Isolated yield for palladium acetate.