Palladium-Catalyzed <i>N</i>‑Allylic\nAlkylation of Pyrazoles and Unactivated Vinylcyclopropanes

An efficient palladium-catalyzed <i>N</i>-allylic\nalkylation\nof pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording\nvarious <i>N</i>-alkyl pyrazoles in ≤99% yield. This\nprotocol displays high atom economy, a broad range of substrates,\nand excellent regioselectivity and stereoselectivity. Late-stage modification\nof bioactive molecules, scaled-up reaction, and divergent derivatization\ndocumented the practicability of this methodology. The preliminary\nmechanistic investigation hinted that the Pd–H species promotes\nthe ring opening of cyclopropanes.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/acs.orglett.4c03808.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Palladium-Catalyzed N‑Allylic\nAlkylation of Pyrazoles and Unactivated Vinylcyclopropanes

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Mycorrhizal Fungi and Plant Interactions
article

Palladium-Catalyzed N‑Allylic\nAlkylation of Pyrazoles and Unactivated Vinylcyclopropanes

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Abstract

An efficient palladium-catalyzed <i>N</i>-allylic\nalkylation\nof pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording\nvarious <i>N</i>-alkyl pyrazoles in ≤99% yield. This\nprotocol displays high atom economy, a broad range of substrates,\nand excellent regioselectivity and stereoselectivity. Late-stage modification\nof bioactive molecules, scaled-up reaction, and divergent derivatization\ndocumented the practicability of this methodology. The preliminary\nmechanistic investigation hinted that the Pd–H species promotes\nthe ring opening of cyclopropanes.

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Mycorrhizal Fungi and Plant Interactions
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Palladium-Catalyzed <i>N</i>‑Allylic\nAlkylation of Pyrazoles and Unactivated Vinylcyclopropanes · Figshare (2024) | TGRS Research Map | TGRS