1: Pd(dba)2; Ph3As; CuI / 1-methyl-pyrrolidin-2-one / 10 h / 50 °C 2: 380 mg / Pd(OAc)2; PPh3; CO / acetonitrile / 15 h / 70 °C / 3040 Torr 3: 91 percent / ammonium formate / Pd(OH)2/C / methanol / 3.5 h / Heating View Scheme

1: bromobenzene With tert.-butyl lithium in tetrahydrofuran T=-78°C; 0.5 h; Inert atmosphere; 2: With bromo(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)dimethylgermane in tetrahydrofuran T=-78°C; 16 h; Inert atmosphere; 3: 1-benzyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate; acetonitrile Further stages;

tetrakis(triphenylphosphine) palladium(0); thallium(I) hydroxide; lithium bromide in tetrahydrofuran; water T=20°C; Suzuki cross-coupling reaction; 48 h; Inert atmosphere;

1: Pd(dba)2; Ph3As; CuI / 1-methyl-pyrrolidin-2-one / 10 h / 50 °C 2: 380 mg / Pd(OAc)2; PPh3; CO / acetonitrile / 15 h / 70 °C / 3040 Torr 3: 91 percent / ammonium formate / Pd(OH)2/C / methanol / 3.5 h / Heating View Scheme

1: bromobenzene With tert.-butyl lithium in tetrahydrofuran T=-78°C; 0.5 h; Inert atmosphere; 2: With bromo(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)dimethylgermane in tetrahydrofuran T=-78°C; 16 h; Inert atmosphere; 3: 1-benzyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate chemoselective reactionFurther stages;