1: sodium hydrogencarbonate / toluene / 4 h / 20 °C / |Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 6.42 h / 0 - 80 °C / |Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 10 h / 80 °C / |Inert atmosphere; |Sealed tube 4: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 24 h / 100 - 110 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

1: 72 percent / ethanol / 2 h / Heating 2: 83 percent / NaBH4 / ethanol / 3 h / Heating 3: lithium diisopropylamide (LDA) / tetrahydrofuran 4: MnO2 / CHCl3 View Scheme

1: 93 percent / pyridine / 0.5 h / 0 °C 2: KOH / acetone / 0.33 h / Heating 3: 60 mg / aq. NaOH / ethanol / 0.17 h / Heating 4: 293 mg / Et3N / CH2Cl2 / 0.5 h / 20 °C 5: 81 percent / Bu3P; 1,3-bis-(diphenylphosphino)propane; iPr2NEt / Pd(OAc)2 / dimethylformamide / 0.5 h / Heating View Scheme

1: sodium hydrogencarbonate / toluene / 4 h / 20 °C / |Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 6.42 h / 0 - 80 °C / |Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 10 h / 80 °C / |Inert atmosphere; |Sealed tube 4: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 24 h / 100 - 110 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

1.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 1 h / Heating 1.2: 78 percent / NEt3 / CH2Cl2 / 5 h / 20 °C 2.1: 75 percent / NaH / dimethylformamide / 2 h / 20 °C 3.1: 50 percent / Pd(OAc)2; DPPP; K2CO3 / dimethylformamide / 8 h / Heating 4.1: 84 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C View Scheme

1: 93 percent / pyridine / 0.5 h / 0 °C 2: KOH / acetone / 0.33 h / Heating 3: 60 mg / aq. NaOH / ethanol / 0.17 h / Heating 4: 578 mg / Et3N / CHCl3 / 12 h / 20 °C 5: 93 percent / Bu3P; 1,3-bis-(diphenylphosphino)propane; iPr2Net / Pd(OAc)2 / dimethylformamide / 0.5 h / Heating View Scheme

1: 84 percent / benzene / 1 h / Heating 2: 58 percent / NaBH4 / dimethylformamide / 1 h / 110 °C 3: 29 percent / NaOH / benzene; H2O; methanol / 2.5 h / Irradiation View Scheme