(SIPr)Pd(cinnanmyl)Cl; potassium tert-butylate in ethylene glycol dimethyl ether T=20°C; Buchwald-Hartwig reaction; 1 h;

potassium carbonate; acetic acid in ethanol T=20°C; 48 h; Heating;

triethylamine in tetrahydrofuran 72 h; RefluxInert atmosphere;

tert-butyl N,N,N',N'-tetraisopropylphosphorodiamidite; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate in toluene T=105°C; Buchwald-Hartwig Coupling; 20 h; Inert atmosphereSchlenk technique;

hydrogen; palladium on activated charcoal in ethanol T=45°C; P=750.06 Torr; 0.5 h; other palladium-containing catalysts; other aldehydes; var. temperatures; Product distribution;

2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one in dichloromethane T=20°C;

1.1: 92 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one / CH2Cl2 / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: tetrahydrofuran; hexane / -78 - 20 °C 2.3: 55 percent / hydrochloric acid / tetrahydrofuran; hexane / 6 h View Scheme