boron tribromide in dichloromethane T=-78 - 20°C; 15.5 h; Inert atmosphere;

Cp*Rh(OTf)2; copper diacetate; potassium carbonate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane in o-xylene T=130°C; 24 h; Inert atmosphere;

sodium hydroxide 1.5 h; Heating;

1: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / toluene / 26 h / 100 °C 2: palladium diacetate; potassium carbonate; 2,2,2-trimethylacetic acid / 24 h / 100 °C 3: boron tribromide / dichloromethane / 15.5 h / -78 - 20 °C View Scheme

1: palladium diacetate; potassium carbonate; 2,2,2-trimethylacetic acid / 24 h / 100 °C 2: boron tribromide / dichloromethane / 15.5 h / -78 - 20 °C View Scheme

1: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / toluene / 26 h / 100 °C 2: palladium diacetate; potassium carbonate; 2,2,2-trimethylacetic acid / 24 h / 100 °C 3: boron tribromide / dichloromethane / 15.5 h / -78 - 20 °C View Scheme

1: iron; acetic acid / 4 h / 45 °C / |Inert atmosphere 2: caesium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 16 h / |Inert atmosphere; |Reflux 3: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / 23 h / 85 °C / |Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / methanol; dichloromethane / 72 h / 20 °C / |Inert atmosphere View Scheme

1: potassium carbonate / acetone / 2 h / |Inert atmosphere; |Reflux 2: iron; acetic acid / 4 h / 45 °C / |Inert atmosphere 3: caesium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 16 h / |Inert atmosphere; |Reflux 4: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / 23 h / 85 °C / |Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / methanol; dichloromethane / 72 h / 20 °C / |Inert atmosphere View Scheme

1: iron; acetic acid / 3.5 h / 45 °C / |Inert atmosphere 2: caesium carbonate; palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine / toluene / 26 h / 100 °C / |Inert atmosphere 3: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / toluene / 31.5 h / 100 °C / |Inert atmosphere 4: boron tribromide / dichloromethane / 15.5 h / -78 - 20 °C / |Inert atmosphere View Scheme

1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 16 h / 95 °C 2: Cp*Rh(OTf)2; copper diacetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; potassium carbonate / o-xylene / 24 h / 130 °C / |Inert atmosphere View Scheme