1: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 2: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 2: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 3: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme

1.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C 1.2: 71 percent / Pd(OAc)2; Buchwald ligand; K3PO4 / tetrahydrofuran / 18 h / 65 °C 2.1: LiBH4 / diethyl ether / 8 h / 0 °C 2.2: (COCl)2; Et3N; DMSO / CH2Cl2 / 6 h / -78 - 0 °C 2.3: 41 percent / CHI3; CrCl2 / tetrahydrofuran / 6 h / 23 °C 3.1: CuI; Pd(Ph3P)4; n-BuNH2 / benzene / 5 h / 23 °C 3.2: 61 percent / H2 / P-2 Ni / ethanol / 1.5 h / 760.05 Torr 4.1: 82 percent / n-Bu4NF / tetrahydrofuran / 8 h / 0 °C 5.1: 90 percent / NaOH / tetrahydrofuran; H2O / 7 h / 23 °C View Scheme

1.1: CuI; Pd(Ph3P)4; n-BuNH2 / benzene / 5 h / 23 °C 1.2: 61 percent / H2 / P-2 Ni / ethanol / 1.5 h / 760.05 Torr 2.1: 82 percent / n-Bu4NF / tetrahydrofuran / 8 h / 0 °C 3.1: 90 percent / NaOH / tetrahydrofuran; H2O / 7 h / 23 °C View Scheme

1.1: LiBH4 / diethyl ether / 8 h / 0 °C 1.2: (COCl)2; Et3N; DMSO / CH2Cl2 / 6 h / -78 - 0 °C 1.3: 41 percent / CHI3; CrCl2 / tetrahydrofuran / 6 h / 23 °C 2.1: CuI; Pd(Ph3P)4; n-BuNH2 / benzene / 5 h / 23 °C 2.2: 61 percent / H2 / P-2 Ni / ethanol / 1.5 h / 760.05 Torr 3.1: 82 percent / n-Bu4NF / tetrahydrofuran / 8 h / 0 °C 4.1: 90 percent / NaOH / tetrahydrofuran; H2O / 7 h / 23 °C View Scheme

1: 82 percent / n-Bu4NF / tetrahydrofuran / 8 h / 0 °C 2: 90 percent / NaOH / tetrahydrofuran; H2O / 7 h / 23 °C View Scheme