1: With piperidine; formic acid; tetrakis(triphenylphosphine) palladium(0) in DMF (N,N-dimethyl-formamide) T=75°C; Heck Reaction; 48 h; 2: With trifluoroacetic acid in dichloromethane T=20°C; 3 h;

1: 1.) magnesium, 2.) (Ph3P)4Pd / 1.) THF, 2.) THF, benzene, room temperature, 10 h 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, -78 deg C 3: 81 percent / hydrogen / PtO2 / dioxane / 20 h / 760 Torr / Ambient temperature 4: 1.) LiH2NBH3, 2.) Na2CO3 / 1.) THF, hexane, room temperature, 3 h, 2.) THF, hexane, water, CHCl3, room temperature, 1 h 5: 85 percent / molybdenum hexacarbonyl / acetonitrile; H2O / 3 h / Heating 6: 42 percent / triphenylphosphine, carbon tetrabromide / acetonitrile / 0.75 h / 70 °C 7: 96 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 8: 97 percent / CHCl3 / 72 h / Heating View Scheme

1.1: 8.4 g / LiAlH4 / tetrahydrofuran / 3 h / 0 °C 2.1: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C 3.1: 81 percent / LiCl; i-Pr2EtN / acetonitrile / 1 h 4.1: Me2AlCl / CH2Cl2; toluene / -78 °C 4.2: 79 percent / CH2Cl2; toluene / 0.25 h / -78 °C 5.1: 84 percent / Sm(OTf)3 / 12 h / 60 °C 6.1: 98 percent / DMAP; Et3N / CH2Cl2 / 3 h 7.1: 81 percent / n-Bu4NF; H2O / tetrahydrofuran / 14 h 8.1: 99 percent / H2O / dimethylsulfoxide / 24 h / 130 °C 9.1: Me3SiOK / toluene / 2 h / 70 °C 9.2: 72 percent / NH4Cl / toluene; H2O 10.1: 70 percent / Pb(OAc)4 / 3 h / 50 °C 11.1: NaBH4 / methanol / 1 h / -40 °C 12.1: 94 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C 13.1: 95 percent / TFA / CH2Cl2 14.1: CHCl3 / Heating View Scheme

1.1: 81 percent / LiCl; i-Pr2EtN / acetonitrile / 1 h 2.1: Me2AlCl / CH2Cl2; toluene / -78 °C 2.2: 79 percent / CH2Cl2; toluene / 0.25 h / -78 °C 3.1: 84 percent / Sm(OTf)3 / 12 h / 60 °C 4.1: 98 percent / DMAP; Et3N / CH2Cl2 / 3 h 5.1: 81 percent / n-Bu4NF; H2O / tetrahydrofuran / 14 h 6.1: 99 percent / H2O / dimethylsulfoxide / 24 h / 130 °C 7.1: Me3SiOK / toluene / 2 h / 70 °C 7.2: 72 percent / NH4Cl / toluene; H2O 8.1: 70 percent / Pb(OAc)4 / 3 h / 50 °C 9.1: NaBH4 / methanol / 1 h / -40 °C 10.1: 94 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C 11.1: 95 percent / TFA / CH2Cl2 12.1: CHCl3 / Heating View Scheme

1.1: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 0 °C 2.1: 81 percent / LiCl; i-Pr2EtN / acetonitrile / 1 h 3.1: Me2AlCl / CH2Cl2; toluene / -78 °C 3.2: 79 percent / CH2Cl2; toluene / 0.25 h / -78 °C 4.1: 84 percent / Sm(OTf)3 / 12 h / 60 °C 5.1: 98 percent / DMAP; Et3N / CH2Cl2 / 3 h 6.1: 81 percent / n-Bu4NF; H2O / tetrahydrofuran / 14 h 7.1: 99 percent / H2O / dimethylsulfoxide / 24 h / 130 °C 8.1: Me3SiOK / toluene / 2 h / 70 °C 8.2: 72 percent / NH4Cl / toluene; H2O 9.1: 70 percent / Pb(OAc)4 / 3 h / 50 °C 10.1: NaBH4 / methanol / 1 h / -40 °C 11.1: 94 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C 12.1: 95 percent / TFA / CH2Cl2 13.1: CHCl3 / Heating View Scheme

1: 94 percent / Et3N / CH2Cl2 / 0.33 h / 0 °C 2: 95 percent / TFA / CH2Cl2 3: CHCl3 / Heating View Scheme

1: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, -78 deg C 2: 81 percent / hydrogen / PtO2 / dioxane / 20 h / 760 Torr / Ambient temperature 3: 1.) LiH2NBH3, 2.) Na2CO3 / 1.) THF, hexane, room temperature, 3 h, 2.) THF, hexane, water, CHCl3, room temperature, 1 h 4: 85 percent / molybdenum hexacarbonyl / acetonitrile; H2O / 3 h / Heating 5: 42 percent / triphenylphosphine, carbon tetrabromide / acetonitrile / 0.75 h / 70 °C 6: 96 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 7: 97 percent / CHCl3 / 72 h / Heating View Scheme

1: 81 percent / hydrogen / PtO2 / dioxane / 20 h / 760 Torr / Ambient temperature 2: 1.) LiH2NBH3, 2.) Na2CO3 / 1.) THF, hexane, room temperature, 3 h, 2.) THF, hexane, water, CHCl3, room temperature, 1 h 3: 85 percent / molybdenum hexacarbonyl / acetonitrile; H2O / 3 h / Heating 4: 42 percent / triphenylphosphine, carbon tetrabromide / acetonitrile / 0.75 h / 70 °C 5: 96 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 6: 97 percent / CHCl3 / 72 h / Heating View Scheme

1: (R,R)-bis(α-methylbenzyl)amine hydrochloride; BuLi / tetrahydrofuran; dimethylformamide; hexane / 4 h / -45 °C 2: 83 percent / NaBH4 / methanol / 2.5 h / -98 - -60 °C 3: Et3N / CH2Cl2 / 4 h / 20 °C 4: TFA / CH2Cl2 / 15 h / 20 °C 5: 26.5 mg / CHCl3 / 60 h / Heating View Scheme

1: 83 percent / NaBH4 / methanol / 2.5 h / -98 - -60 °C 2: Et3N / CH2Cl2 / 4 h / 20 °C 3: TFA / CH2Cl2 / 15 h / 20 °C 4: 26.5 mg / CHCl3 / 60 h / Heating View Scheme