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Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides

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https://hdl.handle.net/10037/13140
DOI
https://doi.org/10.1002/anie.201610520
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Accepted manuscript version (PDF)
Date
2017-03-20
Type
Journal article
Tidsskriftartikkel
Peer reviewed

Author
Vaitla, Janakiram; Bayer, Annette; Hopmann, Kathrin Helen
Abstract
Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Brønsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N−H or C−H functionalization of an aniline or enamine, respectively, and a final acid‐catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
Description
Accepted manuscript version. Published version available at https://doi.org/10.1002/anie.201610520.
Publisher
Wiley
Citation
Vaitla, J., Bayer, A. & Hopmann, K.H. (2017). Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides. Angewandte Chemie International Edition, 56(15), 4277-4281. https://doi.org/10.1002/anie.201610520
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