1: 10-undecylenic acid methyl ester With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; 3 h; 2: (4-bromophenyl)(4-methylphenyl)methanone With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate in tetrahydrofuran; water; N,N-dimethyl-formamide T=20°C; 22 h;

aluminium trichloride in dichloromethane Friedel-Crafts reaction; 1 h; Heating;

1.1: 89 percent / AlCl3 / 3 h / Heating 2.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C 2.2: 93 percent / Cs2CO3; Ph3As; Pd(dppf)Cl2 / dimethylformamide; tetrahydrofuran; H2O / 22 h / 20 °C View Scheme

1.1: AlCl3 / CH2Cl2 / 2 h / 5 - 20 °C 1.2: 61 percent / CH2Cl2 / 20 h / 20 °C 2.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C 2.2: 93 percent / Cs2CO3; Ph3As; Pd(dppf)Cl2 / dimethylformamide; tetrahydrofuran; H2O / 22 h / 20 °C View Scheme

1.1: 94 percent / K2CO3 / acetone / 40 h / 20 °C 2.1: CuI / tetrahydrofuran / 0 °C 2.2: 80 percent / tetrahydrofuran / 96 h 3.1: 23 percent / AlCl3 / CH2Cl2 / 1 h / Heating View Scheme

1.1: CuI / tetrahydrofuran / 0 °C 1.2: 80 percent / tetrahydrofuran / 96 h 2.1: 23 percent / AlCl3 / CH2Cl2 / 1 h / Heating View Scheme

1.1: CuI / tetrahydrofuran / 0 °C 1.2: 80 percent / tetrahydrofuran / 96 h 2.1: 23 percent / AlCl3 / CH2Cl2 / 1 h / Heating View Scheme

1.1: 89 percent / AlCl3 / 3 h / Heating 2.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C 2.2: 93 percent / Cs2CO3; Ph3As; Pd(dppf)Cl2 / dimethylformamide; tetrahydrofuran; H2O / 22 h / 20 °C View Scheme

1.1: sulfuric acid / Reflux 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.2: 22 h / 20 °C / Inert atmosphere View Scheme