1.1: 71 percent / Bu3SnH; α,α'-azobis(isobutyronitrile); methyllithium / benzene 2.1: 84 percent / triethylamine / DMAP / tetrahydrofuran / 0 - 20 °C 3.1: Bu3SnH; α,α'-azobis(isobutyronitrile) / benzene / 7.5 h 3.2: 38 percent / methyllithium / benzene / 12 h / 20 °C View Scheme

azobisisobutyronitrile; methyllithium; tri-n-butyl-tin hydride in benzene desilylation;

1.1: 71 percent / Bu3SnH; α,α'-azobis(isobutyronitrile); methyllithium / benzene 2.1: 84 percent / triethylamine / DMAP / tetrahydrofuran / 0 - 20 °C 3.1: Bu3SnH; α,α'-azobis(isobutyronitrile) / benzene / 7.5 h 3.2: 50 percent / methyllithium / benzene / 12 h / 20 °C View Scheme