pyridinium p-toluenesulfonate in tetrahydrofuran; water T=0°C; 72 h; Inert atmosphere;

1: 78 percent / H2; quinoline / Lindlad's catalyst / ethanol / 16 h / 23 °C / 760 Torr 2: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 3: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 4: 90 percent / tetrahydrofuran / 0 - 23 °C 5: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme

toluene-4-sulfonic acid in tetrahydrofuran; water

1: 281.6 mg / 0.5 h / 20 °C 2: 80 percent / H2; quinoline / Pd/CaCO3; Pb / ethanol / 3 h / 20 °C 3: 30.4 mg / DIPEA; HATU / acetonitrile / 0.5 h / 20 °C 4: DBU / dimethylformamide / 60 h / 20 °C 5: 16.2 mg / TBAF; AcOH / tetrahydrofuran / 0.25 h / 0 °C 6: TsOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

in 1,2-dichloro-ethane T=23°C; 10 - 11 h; Product distribution / selectivity;

1: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 2: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 3: 90 percent / tetrahydrofuran / 0 - 23 °C 4: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme

1: 100 percent / NaClO2; NaH2PO4; 2-methyl-2-butene / H2O; butan-1-ol / 0.33 h / 23 °C 2: 78 percent / H2; quinoline / Lindlad's catalyst / ethanol / 16 h / 23 °C / 760 Torr 3: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 4: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 5: 90 percent / tetrahydrofuran / 0 - 23 °C 6: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme

1: 86 percent / Ag2O / dimethylformamide / 21 h / 23 °C 2: 98 percent / Grubbs' 2nd catalyst / benzene / 0.5 h / Heating 3: 72 percent / pyridinium dichromate / 1,2-dichloro-ethane / 8 h / Heating 4: 98 percent / H2 / PtO2 / ethanol / 3 h / 23 °C 5: 96 percent / tetrahydrofuran / 1.5 h / -78 °C 6: 39 percent / Et3SiH; BF3*OEt2 / CH2Cl2; 2,2,2-trifluoro-ethanol / 3 h / -78 °C 7: TFA / CH2Cl2 / 0 - 23 °C 8: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 9: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 10: 90 percent / tetrahydrofuran / 0 - 23 °C 11: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme

1.1: O3 / methanol / 0.05 h / -78 °C 1.2: 81 percent / methylsulfide / methanol / 2 h / -78 - 23 °C 2.1: 100 percent / NaClO2; NaH2PO4; 2-methyl-2-butene / H2O; butan-1-ol / 0.33 h / 23 °C 3.1: 78 percent / H2; quinoline / Lindlad's catalyst / ethanol / 16 h / 23 °C / 760 Torr 4.1: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 5.1: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 6.1: 90 percent / tetrahydrofuran / 0 - 23 °C 7.1: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme

1: 96 percent / camphorsulfonic acid / methanol / 6 h / 23 °C 2: 86 percent / Ag2O / dimethylformamide / 21 h / 23 °C 3: 98 percent / Grubbs' 2nd catalyst / benzene / 0.5 h / Heating 4: 72 percent / pyridinium dichromate / 1,2-dichloro-ethane / 8 h / Heating 5: 98 percent / H2 / PtO2 / ethanol / 3 h / 23 °C 6: 96 percent / tetrahydrofuran / 1.5 h / -78 °C 7: 39 percent / Et3SiH; BF3*OEt2 / CH2Cl2; 2,2,2-trifluoro-ethanol / 3 h / -78 °C 8: TFA / CH2Cl2 / 0 - 23 °C 9: 86 percent / N,N-diisopropylethylamine; HATU / acetonitrile / 12 h / 23 °C 10: 67 percent / Grela's catalyst / CH2Cl2 / 9 h / 23 °C 11: 90 percent / tetrahydrofuran / 0 - 23 °C 12: 28 percent / Grela's catalyst / 1,2-dichloro-ethane / 10 h / 23 °C View Scheme