Visible Light Photoredox Catalyzed Cascade Cyclizations of α-Bromochalcones or α-Bromocinnamates with Heteroarenes

Authors

  • Suva Paria,

    1. Institut für Organische Chemie, Universität Regensburg Universitätsstrasse 31, 93053 Regensburg, Germany, Fax: (+49)-941-943-4121; phone: (+49)-941-943-4631
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  • Oliver Reiser

    Corresponding author
    1. Institut für Organische Chemie, Universität Regensburg Universitätsstrasse 31, 93053 Regensburg, Germany, Fax: (+49)-941-943-4121; phone: (+49)-941-943-4631
    • Institut für Organische Chemie, Universität Regensburg Universitätsstrasse 31, 93053 Regensburg, Germany, Fax: (+49)-941-943-4121; phone: (+49)-941-943-4631

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Abstract

Vinyl radicals were generated from α-bromochalcones or α-bromocinnamate ethyl ester under visible light photoredox catalyzed conditions via an oxidative quenching cycle of the iridium complex [Ir{dF(CF3)ppy}2(dtbbpy)]PF6 and subjected to cascade cyclizations with heteroarenes entailing two consecutive C[BOND]C bond formations and three C[BOND]H activations. The process is amenable to furans, benzofurans, pyrroles, and indoles, giving rise to a broad variety of novel polycyclic frameworks in high yields under mild and environmentally benign reaction conditions.

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