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Ionic liquids, microwave irradiation, and the synthesis of aryl Weinreb amides

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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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Acknowledgements

AAO thanks the Saudi Arabian government for the provision of a PhD scholarship. AM acknowledges project funding from the Australian Research Council.

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Authors and Affiliations

  1. Department of Chemistry, School of Environmental and Life Sciences, University Drive, Callaghan, NSW, 2308, Australia

    Ahmed Al Otaibi & Adam McCluskey

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  1. Ahmed Al Otaibi
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  2. Adam McCluskey
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Correspondence to Adam McCluskey.

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Otaibi, A.A., McCluskey, A. Ionic liquids, microwave irradiation, and the synthesis of aryl Weinreb amides. Monatsh Chem 149, 519–525 (2018). https://doi.org/10.1007/s00706-017-2089-3

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  • DOI: https://doi.org/10.1007/s00706-017-2089-3

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