1.1: methanol; sodium tetrahydroborate / tert-butyl alcohol / Reflux 2.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 3.1: triphenylphosphine; nickel dichloride; zinc / acetonitrile / 0.5 h / 20 °C 3.2: 8 h / Reflux View Scheme

1.1: methanol; sodium tetrahydroborate / tert-butyl alcohol / Reflux 2.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 3.1: triphenylphosphine; nickel dichloride; zinc / acetonitrile / 0.5 h / 20 °C 3.2: 8 h / Reflux 4.1: sodium hydride / dimethyl sulfoxide; paraffin oil / 0.17 h / 20 °C / Inert atmosphere 4.2: 0.83 h / 40 °C View Scheme