First catalytic and green synthesis of aryl-(Z)-vinyl chlorides and its plausible addition-elimination mechanism.

Via a catalytic cycle in the presence of scandium triflate (2 mol %)/DMF (1 mol %)/benzoyl chloride (5 mol %), aromatic ketones were treated with bis(trichloromethyl) carbonate (BTC) to afford aryl-(Z)-vinyl chlorides. All metal triflates tested in the reaction showed highly catalytic activity. A plausible addition-elimination mechanism was proposed. The present work describes the first catalytic and green route to the synthesis of aryl-(Z)-vinyl chlorides. [reaction: see text]