aluminium trichloride in dichloromethane T=0°C; 0.25 h;

1: 93 percent / PdCl2(dppf) / tetrahydrofuran / 15 h / Heating 2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 1.) n-BuLi, TMEDA / 1.) hexane, 45 deg C, 30 min, 2.) THF, 55-60 deg C, 20 h 2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 1.) n-BuLi, TMEDA / 1.) hexane, 45 deg C, 30 min, 2.) THF, 55-60 deg C, 20 h 2: 97 percent / AlCl3 / CH2Cl2 / 0.25 h / 0 °C View Scheme

sulfuric acid

2: aq. H2SO4 View Scheme

1: (i) Na, EtOH, (ii) KOH, ethane-1,2-diol, (iii) (heating) 2: H2SO4 4: aq. H2SO4 View Scheme

1: H2SO4 3: aq. H2SO4 View Scheme

1: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C 2: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h 3: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr 4: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h 5: 64 percent / benzene / 24 h / Ambient temperature; Irradiation 6: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C View Scheme

1: 95 percent / BBr3 / CH2Cl2 / 4 h / -78 - 25 °C 2: 87 percent / DMAP / pyridine / 1.) 0 deg C -> 25 deg C, 1 h, 2.) 25 deg C, 48 h 3: 71 percent / LiCl, 4A sieves, Me4Sn, 2,6-di-tert-butylhydroxytoluene / PdCl2(dppf) / dimethylformamide / 12 h / 90 °C / 2585.7 Torr 4: 1.) LiHMDS, 2,2,2-trifluoroethyl trifluoroacetate, 2.) MsN3, Et3N / 1.) THF, -78 deg C, 45 min, 2.) MeCN, H2O, 25 deg C, 6 h 5: 64 percent / benzene / 24 h / Ambient temperature; Irradiation 6: 84 percent / n-Bu4NF, O2 / tetrahydrofuran / 40 h / 25 °C 7: 100 percent / conc. H2SO4 / ethanol / 0.75 h / 25 °C View Scheme