1: CH2Cl2 / -20 °C 2: 72 percent / chlorobenzene / 3 h / Heating 3: 92 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 760 Torr / Ambient temperature 4: 78 percent / LiBH4, B-methoxy-9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 14 h / Ambient temperature 5: 82 percent / Et3N / CH2Cl2 / 20 h / Ambient temperature 6: 33 percent / KH, MeOH / tetrahydrofuran / 20 h / Heating 7: 1) KOH, 2) CuCl, NH4OH / 1) iPrOH, reflux, 14 h, 2) H2O 8: benzene-d6 / 0.05 h / Irradiation View Scheme

1: 92 percent / H2 / 10percent Pd/C / ethyl acetate / 14 h / 760 Torr / Ambient temperature 2: 78 percent / LiBH4, B-methoxy-9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 14 h / Ambient temperature 3: 82 percent / Et3N / CH2Cl2 / 20 h / Ambient temperature 4: 33 percent / KH, MeOH / tetrahydrofuran / 20 h / Heating 5: 1) KOH, 2) CuCl, NH4OH / 1) iPrOH, reflux, 14 h, 2) H2O 6: benzene-d6 / 0.05 h / Irradiation View Scheme

T=253°C; Ea; var. temp.; Product distributionThermodynamic data;

T=253°C; Ea; var. temp.; Product distributionThermodynamic data;