1: 1-bromo-2-methoxy-naphthalene With magnesium in tetrahydrofuran T=20 - 50°C; 1 h; Inert atmosphereSchlenk technique; 2: boric acid trimethyl ester in tetrahydrofuran T=-78°C; 2 h; Inert atmosphereSchlenk technique;

1: With magnesium in tetrahydrofuran T=20 - 50°C; 3 h; 2: With boric acid trimethyl ester in tetrahydrofuran T=-78 - 20°C;

Mg in tetrahydrofuran addn. of BrC10H6OMe/THF to Mg (activated by stirring for 24 h under Ar at r.t.); stirring at room temp. for 2 h and then at 50°C for 1h; cooling to -78°C, addn. B(OC4H9)3 (cooled at -78°C for 2h); warming to r.t., stirring overnight; addn. of H2O with stirring; evapn. in vac., acidifying with HCl; extn. of aq. soln. with CH2Cl2; combining of org. layer; drying over anhyd. MgSO4, filtration, concn., resuspending in CH2Cl2 with stirring for 0.5 h; filtration, washing with cold CH2Cl2;

1.1: 94 percent / aq. NaOH; aliquat 336 / CH2Cl2 / 20 °C 2.1: Mg / tetrahydrofuran / 3 h / 20 - 50 °C 2.2: 80 percent / B(OMe)3 / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: bromine / acetic acid / 20 °C 2.1: magnesium / tetrahydrofuran / 2 h / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere View Scheme

(R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride in tetrahydrofuran Suzuki-Miyaura Coupling; 72 h; RefluxInert atmosphere; Overall yield = 90 percent; enantioselective reaction;

cesium fluoride; cyclopalladated [1-(p-tolylimino)ethyl]ferrocene catalyst in 1,4-dioxane T=100°C; Suzuki coupling; 20 h;

1.1: tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether / 0.5 h 1.2: |Reflux 2.1: boron tribromide / dichloromethane / 20 °C / |Reflux 3.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 4.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Heating 4.2: 40 h / 100 °C View Scheme

(R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride in tetrahydrofuran Suzuki-Miyaura Coupling; 72 h; RefluxInert atmosphere; Overall yield = 90 percent; enantioselective reaction;

CpPd(SIPr)Cl; potassium tert-butylate in isopropyl alcohol T=25°C; 24 h; Inert atmosphere;