Potassium Phosphate, Tribasic → 2'-Phenyl-2,4,6-trimethylbiphenyl

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To a mixture of biphenyl-2-ylboronic acid (0.15 g, 0.75 mmol, 1.5 equiv) and 2-bromo-1,3,5-trimethylbenzene (100 mg, 0.5 mmol, 1.0 equiv), tris(dibenzylideneacetone)dipalladium (0.46 mg, 0.0005 m mol, 0.1 mol %), 3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole (0.66 mg, 0.04 mmol, 0.4 mol %), and potassium phosphate (0.318 g, 1.5 mmol, 3 equiv) was charged dagassed toluene (4 mL). The mixture was stirred at 70° C. under nitrogen for 3 h, then quenched with water (4 mL). The organic phase was separated, washed with brine, dried over sodium sulfate, concentrated, and purified by column chromatography to provide pure desired product as oil (129 mg, 0.48 mmol, 95%). ESI-MS: m/z 273 [M+H]+.

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