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Journal Article

Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles

MPS-Authors

Zhang,  Pinglu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Tsuji,  Nobuya
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ouyang,  Jie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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jacs.0c12042.pdf
(Postprint), 2MB

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Citation

Zhang, P., Tsuji, N., Ouyang, J., & List, B. (2021). Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles. Journal of the American Chemical Society, 143(2), 675-680. doi:10.1021/jacs.0c12042.


Cite as: http://hdl.handle.net/21.11116/0000-0007-CE93-B
Abstract
In recent years, several organocatalytic asymmetric hydroarylations of activated, electron-poor olefins with activated, electron-rich arenes have been described. In contrast, only a few approaches that can handle unactivated, electronically neutral olefins have been reported and invariably require transition metal catalysts. Here we show how an efficient and highly enantioselective catalytic asymmetric intramolecular hydroarylation of aliphatic and aromatic olefins with indoles can be realized using strong and confined IDPi Brønsted acid catalysts. This unprecedented transformation is enabled by tertiary carbocation formation and establishes quaternary stereogenic centers in excellent enantioselectivity and with a broad substrate scope that includes an aliphatic iodide, an azide, and an alkyl boronate, which can be further elaborated into bioactive molecules.