1,3-Difunctionalization\nof Donor–Acceptor Cyclopropanes\nEnabled by Copper Nitrate: A Direct Approach to γ‑Halonitrates

1,3-Difunctionalization of donor–acceptor cyclopropanes\nwith copper nitrate and <i>N</i>-halosuccinimide was developed\nto efficiently afford γ-halonitrates. The pivotal factor of\nthis protocol lies in the dual role of copper nitrate as a Lewis acid\nand an ideal nitrooxy source. The given approach features easy handling,\ngood functional group compatibility, and wide substrate scope. Furthermore,\nvarious transformations of the obtained γ-chloronitrates underscore\nthe remarkable synthetic potential inherent in this method.

Publication Details

Journal
Figshare
Published
2024-10-31
DOI
https://doi.org/10.1021/acs.orglett.4c03370.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

1,3-Difunctionalization\nof Donor–Acceptor Cyclopropanes\nEnabled by Copper Nitrate: A Direct Approach to γ‑Halonitrates

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Cyclopropane Reaction Mechanisms
article

1,3-Difunctionalization\nof Donor–Acceptor Cyclopropanes\nEnabled by Copper Nitrate: A Direct Approach to γ‑Halonitrates

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Abstract

1,3-Difunctionalization of donor–acceptor cyclopropanes\nwith copper nitrate and <i>N</i>-halosuccinimide was developed\nto efficiently afford γ-halonitrates. The pivotal factor of\nthis protocol lies in the dual role of copper nitrate as a Lewis acid\nand an ideal nitrooxy source. The given approach features easy handling,\ngood functional group compatibility, and wide substrate scope. Furthermore,\nvarious transformations of the obtained γ-chloronitrates underscore\nthe remarkable synthetic potential inherent in this method.

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Cyclopropane Reaction Mechanisms
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1,3-Difunctionalization\nof Donor–Acceptor Cyclopropanes\nEnabled by Copper Nitrate: A Direct Approach to γ‑Halonitrates · Figshare (2024) | TGRS Research Map | TGRS