Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2‑Alkylidenecyclobutanol Derivatives: Access to β‑Monofluorinated Cyclopropanecarbaldehydes

Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2‑Alkylidenecyclobutanol Derivatives: Access to β‑Monofluorinated Cyclopropanecarbaldehydes

A hypervalent iodine­(III)-mediated ring-contractive fluorination reaction of 2-alkylidenecyclobutanol derivatives is presented. The protocol allows the facile synthesis of β-monofluorinated cyclopropanecarbaldehydes via a fluorination/semipinacol rearrangement cascade using nucleophilic Py·HF as th...

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Veröffentlicht in:Journal of organic chemistry 2021-05, Vol.86 (9), p.6800-6812
Hauptverfasser: Feng, Si-Xin, Yang, Shuang, Tu, Fang-Hai, Lin, Peng-Peng, Huang, Long-Ling, Wang, Honggen, Huang, Zhi-Shu, Li, Qingjiang
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container_end_page 6812
container_issue 9
container_start_page 6800
container_title Journal of organic chemistry
container_volume 86
creator Feng, Si-Xin
Yang, Shuang
Tu, Fang-Hai
Lin, Peng-Peng
Huang, Long-Ling
Wang, Honggen
Huang, Zhi-Shu
Li, Qingjiang
description A hypervalent iodine­(III)-mediated ring-contractive fluorination reaction of 2-alkylidenecyclobutanol derivatives is presented. The protocol allows the facile synthesis of β-monofluorinated cyclopropanecarbaldehydes via a fluorination/semipinacol rearrangement cascade using nucleophilic Py·HF as the fluorine source. For challenging electron-rich arene substrates, the installation of a protecting group on the free alcohol is pivotal for maintaining the reaction efficiency. The synthetic utility was demonstrated by the scalability of this reaction and further transformations of the products.
doi_str_mv 10.1021/acs.joc.1c00578
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title Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2‑Alkylidenecyclobutanol Derivatives: Access to β‑Monofluorinated Cyclopropanecarbaldehydes
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