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]
Su
Weike
W
College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering, Hangzhou 310014, PRC. suweike@zjut.edu.cn
Jin
Can
C
D001565:Benzoates / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D004126:Dimethylformamide / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012538:Scandium / Q000737:chemistry; D014752:Vinyl Chloride / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D001565:Benzoates; D007659:Ketones; D008698:Mesylates; D009942:Organometallic Compounds; D014753:Vinyl Compounds; C436603:scandium triflate; D004126:Dimethylformamide; C013409:benzoyl chloride; D014752:Vinyl Chloride; D012538:Scandium