The Gomberg–Bachmann Reaction for the Arylation of Anilines with Aryl Diazotates

Authors

  • Gerald Pratsch,

    1. Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany), Fax: (+49) 9131-85-22585
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  • Tina Wallaschkowski,

    1. Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany), Fax: (+49) 9131-85-22585
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  • Prof. Dr. Markus R. Heinrich

    Corresponding author
    1. Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany), Fax: (+49) 9131-85-22585
    • Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen (Germany), Fax: (+49) 9131-85-22585
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Abstract

original image

Simply aqueous sodium hydroxide is sufficient to exclude ionic side reactions and to prepare 2-aminobiphenyls from aryl diazotates and anilines through a new variant of the Gomberg–Bachmann reaction (see scheme). The metal-free reaction under basic conditions allows to exploit the highly radical-stabilizing effect of the aniline's free amino function for the first time, which leads to a so far unreached regioselectivity.

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