Palladium Precatalyst for Buchwald–Hartwig Coupling of Bulky Substrates

Palladium Precatalyst for Buchwald–Hartwig Coupling of Bulky Substrates

Bromo[4-(trifluoromethyl)phenyl][tris(1,1-dimethylethyl)phosphine]palladium, or Pd(PtBu3)(4-C6H4CF3)Br [B7081], is a palladium precatalyst for Buchwald–Hartwig coupling reactions. It is a solid that is stable to air and moisture, which makes it easy to handle. It can be used for coupling reactions involving substrates bearing bulky substituents, which are usually difficult to react. In the TCI example, 2-bromo-1,3,5-triisopropylbenzene was coupled with 2,6-diisopropylaniline using sodium tert-butoxide in toluene at 100 °C for 16 hours, with 1 mol% of the catalyst, giving the product in 89% yield after silica gel chromatography.¹) The reaction was monitored by HPLC, and toluene was degassed beforehand.

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