sodium ethanolate; potassium iodide in tetrahydrofuran T=70°C; 12 h;

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 20 h; Heating;

1: With C23H31AuN(1+)*F6Sb(1-); benzyl alcohol in dichloromethane T=20°C; 1 h; in air; 2: With toluene-4-sulfonic acid in dichloromethane T=40°C; 6 h; in air;

1: 83 percent / thionyl chloride; NaOEt / ethanol / 2 h / Heating 2: 46 percent / titanium tetraisopropoxide; cyclohexylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / 20 °C 3: ferric(III) chloride; pyridine / diethyl ether / 3 h / 0 °C 4: sodium acetate / methanol / 20 °C View Scheme

1: 46 percent / titanium tetraisopropoxide; cyclohexylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / 20 °C 2: ferric(III) chloride; pyridine / diethyl ether / 3 h / 0 °C 3: sodium acetate / methanol / 20 °C View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2.1: C23H31AuN(1+)*F6Sb(1-); benzyl alcohol / dichloromethane / 1 h / 20 °C / in air 2.2: 6 h / 40 °C / in air View Scheme

1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 76 percent / tetrahydrofuran / 0.67 h / -78 °C 2.1: AgTf / 0.67 h / -78 °C View Scheme