1: 84 percent / tetrakis(triphenylphosphane)palladium(0) / tetrahydrofuran / 8 h / Heating 2: 92 percent / phosphoryl chloride / 0.25 h / 50 °C 3: 83 percent / aluminum(III) chloride; tBuNH2-BH3 / CH2Cl2 / 0.5 h / Heating View Scheme

sodium acetate; triphenylphosphine T=140°C; 0.5 h;

1: 92 percent / phosphoryl chloride / 0.25 h / 50 °C 2: 83 percent / aluminum(III) chloride; tBuNH2-BH3 / CH2Cl2 / 0.5 h / Heating View Scheme

1: 94 percent / triethylamine / CH2Cl2 / 0.08 h / 20 °C 2: 61 percent / tetrakis(triphenylphosphane)palladium(0) / tetrahydrofuran / 48 h / Heating 3: 92 percent / phosphoryl chloride / 0.25 h / 50 °C 4: 83 percent / aluminum(III) chloride; tBuNH2-BH3 / CH2Cl2 / 0.5 h / Heating View Scheme

1: 61 percent / tetrakis(triphenylphosphane)palladium(0) / tetrahydrofuran / 48 h / Heating 2: 92 percent / phosphoryl chloride / 0.25 h / 50 °C 3: 83 percent / aluminum(III) chloride; tBuNH2-BH3 / CH2Cl2 / 0.5 h / Heating View Scheme

1: 92 percent / Et3N / CH2Cl2 / 0.17 h / 20 °C 2: 51 percent / phosphorus pentasulfide; sodium hydrogencarbonate / tetrahydrofuran / 3 h / 20 °C 3: 22 percent / sodium acetate; triphenylphosphine / 0.5 h / 140 °C View Scheme

1: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 3: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 4: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: pyridine / 6 h / 20 °C 2: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 °C 3: CuSO4‵5H2O; acetic acid; zinc / water / 2.5 h / 0 °C 4: methanol; sodium methylate / 4 h / 20 °C 5: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 6: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 7: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 8: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 9: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 °C 2: CuSO4‵5H2O; acetic acid; zinc / water / 2.5 h / 0 °C 3: methanol; sodium methylate / 4 h / 20 °C 4: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 5: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 6: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 7: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 8: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 2: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 4: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 5: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme