palladium diacetate; CsO2CCMe3; bis(1,1-diphenylphosphino)methane; tetrabutyl ammonium fluoride in N,N-dimethyl-formamide T=100°C; 24 h;

palladium diacetate; CsO2CCMe3; bis(1,1-diphenylphosphino)methane in N,N-dimethyl-formamide T=100°C; 24 h;

1.1: 85 percent / tetrahydrofuran / 6 h / 80 °C 2.1: 62 percent / t-BuLi; ICH2CH2I / pentane; diethyl ether / 0.5 h / -78 °C 3.1: 91 percent / trifluoroacetic acid / CH2Cl2 / 16 h / 20 °C 4.1: 88 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide; H2O / 3 h / 70 °C 5.1: H2SO4; NaNO2 / H2O; 1,2-dimethoxy-ethane / 0.33 h / 0 °C 5.2: 81 percent / NaI / 1,2-dimethoxy-ethane; H2O / 0.17 h / 0 °C 6.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 100 °C View Scheme

1.1: 88 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide; H2O / 3 h / 70 °C 2.1: H2SO4; NaNO2 / H2O; 1,2-dimethoxy-ethane / 0.33 h / 0 °C 2.2: 81 percent / NaI / 1,2-dimethoxy-ethane; H2O / 0.17 h / 0 °C 3.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 100 °C View Scheme

1.1: H2SO4; NaNO2 / H2O; 1,2-dimethoxy-ethane / 0.33 h / 0 °C 1.2: 81 percent / NaI / 1,2-dimethoxy-ethane; H2O / 0.17 h / 0 °C 2.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 100 °C View Scheme

1.1: 62 percent / t-BuLi; ICH2CH2I / pentane; diethyl ether / 0.5 h / -78 °C 2.1: 91 percent / trifluoroacetic acid / CH2Cl2 / 16 h / 20 °C 3.1: 88 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide; H2O / 3 h / 70 °C 4.1: H2SO4; NaNO2 / H2O; 1,2-dimethoxy-ethane / 0.33 h / 0 °C 4.2: 81 percent / NaI / 1,2-dimethoxy-ethane; H2O / 0.17 h / 0 °C 5.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 100 °C View Scheme

1.1: 91 percent / trifluoroacetic acid / CH2Cl2 / 16 h / 20 °C 2.1: 88 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide; H2O / 3 h / 70 °C 3.1: H2SO4; NaNO2 / H2O; 1,2-dimethoxy-ethane / 0.33 h / 0 °C 3.2: 81 percent / NaI / 1,2-dimethoxy-ethane; H2O / 0.17 h / 0 °C 4.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 100 °C View Scheme

1.1: 88 percent / aq. K2CO3; PdCl2(PPh3)2 / dimethylformamide / 3 h / 70 °C 2.1: aq. H2SO4; NaNO2 / 1,2-dimethoxy-ethane / 0.33 h / 0 °C 2.2: 81 percent / aq. NaI / 1,2-dimethoxy-ethane / 0.17 h / 0 °C 3.1: 88 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / / / dimethylformamide / 24 h / 100 °C View Scheme

1.1: Mg / tetrahydrofuran 1.2: tetrahydrofuran / 14 h / 20 °C 1.3: 40 percent / iodine / tetrahydrofuran / 0.5 h / 20 °C 2.1: 98 percent / BBr3 / CH2Cl2 / -78 - 20 °C 3.1: 46 percent / Cu(OAc)2; triethylamine; oxygen / CH2Cl2 / 48 h / 20 °C / 760 Torr 4.1: 89 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 110 °C View Scheme

1: 98 percent / BBr3 / CH2Cl2 / -78 - 20 °C 2: 46 percent / Cu(OAc)2; triethylamine; oxygen / CH2Cl2 / 48 h / 20 °C / 760 Torr 3: 89 percent / 1,1-bis(diphenylphosphino)methane; CsO2CCMe3; Pd(OAc)2 / dimethylformamide / 24 h / 110 °C View Scheme