1.1: 86 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 2.5 h / 110 °C 2.1: 98 percent / H2 / Pd/C / ethanol / 18 h / 20 °C 3.1: lithium; NH3 / tetrahydrofuran / 0.17 h / -78 °C 3.2: NH4Cl / tetrahydrofuran / -78 - 20 °C View Scheme

sodium hydride; bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in toluene Heating;

1: 89 percent / Et3N / CH2Cl2 2: 86 percent / K2CO3 / acetonitrile / 16 h / Heating 3: 97 percent / NaH / Grubbs I catalyst / toluene / Heating View Scheme

1: 86 percent / K2CO3 / acetonitrile / 16 h / Heating 2: 97 percent / NaH / Grubbs I catalyst / toluene / Heating View Scheme

citric acid in toluene 7 h; Heating;

1: 43 percent / n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C 2: i-Bu2AlH / CH2Cl2; hexane / 3 h / -78 - -40 °C 3: 353 mg / citric acid monohydrate / toluene / 7 h / Heating View Scheme

1: i-Bu2AlH / CH2Cl2; hexane / 3 h / -78 - -40 °C 2: 353 mg / citric acid monohydrate / toluene / 7 h / Heating View Scheme