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Catalyst- and Halogen-Free Regioselective Friedel–Crafts α-Ketoacylations

Authors

  • Dr. Kishor Mohanan,

    1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
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  • Dr. Marc Presset,

    1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
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  • Dr. Damien Mailhol,

    1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
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  • Dr. Yoann Coquerel,

    Corresponding author
    1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
    • Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
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  • Prof. Dr. Jean Rodriguez

    Corresponding author
    1. Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
    • Institut des Sciences Moléculaires de Marseille, UMR CNRS 7313 iSm2, Aix-Marseille Université, Centre Saint Jérôme, Service 531, 13397 Marseille cedex 20 (France), Fax: (+33) 491-289-187
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Abstract

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Fast, efficient and green! Highly regioselective and efficient catalyst- and halogen-free Friedel–Crafts α-ketoacylation reactions leading to heterocycles functionalized with a very versatile 1,3-diketone moiety are described. The reactions rely on microwave-assisted domino Wolff rearrangement/Friedel–Crafts sequences from 2-diazo-1,3-diketones via transient, highly reactive α-keto ketene intermediates.

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