1: 13-tetradecenoic acid methyl ester With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; 4 h; 2: (4-bromophenyl)(4-methylphenyl)methanone With triphenyl-arsane; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran; water; N,N-dimethyl-formamide Suzuki coupling; Heating;

1.1: 98 percent / H2SO4 / Heating 2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 2.2: 2.15 g / Cs2CO3; AsPh3 / Pd(dppf)Cl2 / tetrahydrofuran; dimethylformamide; H2O / Heating View Scheme

1.1: magnesium / tetrahydrofuran / 2 h / 45 °C 1.2: 82 percent / CuCl / tetrahydrofuran / 1 h / 0 °C 2.1: 98 percent / H2SO4 / Heating 3.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 3.2: 2.15 g / Cs2CO3; AsPh3 / Pd(dppf)Cl2 / tetrahydrofuran; dimethylformamide; H2O / Heating View Scheme

1.1: 89 percent / AlCl3 / 3 h / Heating 2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 2.2: 2.15 g / Cs2CO3; AsPh3 / Pd(dppf)Cl2 / tetrahydrofuran; dimethylformamide; H2O / Heating View Scheme

1.1: 89 percent / AlCl3 / 3 h / Heating 2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C 2.2: 2.15 g / Cs2CO3; AsPh3 / Pd(dppf)Cl2 / tetrahydrofuran; dimethylformamide; H2O / Heating View Scheme