Abstract
The Heck coupling of aryl halides and N-methoxy-N-methylacrylamide was investigated in the room-temperature ionic liquids [BMIM][PF6], [BMIM][Br], [BMIM][BF4], [BMIM][OH], [BMIM][HCOO], EAN, PAN, and ETAN. Excellent yields of the expected N-methoxy-N-methylcinnamamides (ca 90%) and purity (> 96%) were afforded on simple diethyl ether extraction from [BMIM][PF6] and [BMIM][OH]. The described procedure was highly substrate tolerant with methyl, methoxy, fluoro, trifluoromethyl, ester, cyano, hydroxy, naphthyl, and quinolone moieties well tolerated. Poor yields or no reactions were observed with -NH2 and -NO2 moieties. The use of microwave irradiation reduced reaction times from 3 h (thermal) to 5-15 min with no substantive effect on reaction outcome.
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