Sequential One-Pot\nTransformation to R–CF<sub>2</sub>‑Embedded 1,5-Diketones\nEnabled by Nickel: Access to\n4‑Perfluoroalkylpyridines

Herein, we have demonstrated the\napplication of bench-stable\npolyfluorinated\nalcohols as fluoroalkylating reagents for a sequential one-pot transformation\nwith ketones to R–CF<sub>2</sub>-embedded 1,5-diketones and\npyridines enabled by a nickel catalyst. The protocol is tolerant to\na range of functional groups (>31 examples and up to 85% yield)\nand\nperfluoro alcohols and releases H<sub>2</sub> and H<sub>2</sub>O as\nbyproducts. Preliminary mechanistic studies, EPR analyses, and deuterium\nscrambling experiments were performed, and observed <i>P</i><sub>C–H</sub>/<i>P</i><sub>C‑D</sub> = 2.12.

Publication Details

Journal
Figshare
Published
2024-10-23
DOI
https://doi.org/10.1021/acs.orglett.4c03478.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
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article

Sequential One-Pot\nTransformation to R–CF2‑Embedded 1,5-Diketones\nEnabled by Nickel: Access to\n4‑Perfluoroalkylpyridines

Figshare
Fluorine in Organic Chemistry
article

Sequential One-Pot\nTransformation to R–CF2‑Embedded 1,5-Diketones\nEnabled by Nickel: Access to\n4‑Perfluoroalkylpyridines

article en

Abstract

Herein, we have demonstrated the\napplication of bench-stable\npolyfluorinated\nalcohols as fluoroalkylating reagents for a sequential one-pot transformation\nwith ketones to R–CF<sub>2</sub>-embedded 1,5-diketones and\npyridines enabled by a nickel catalyst. The protocol is tolerant to\na range of functional groups (>31 examples and up to 85% yield)\nand\nperfluoro alcohols and releases H<sub>2</sub> and H<sub>2</sub>O as\nbyproducts. Preliminary mechanistic studies, EPR analyses, and deuterium\nscrambling experiments were performed, and observed <i>P</i><sub>C–H</sub>/<i>P</i><sub>C‑D</sub> = 2.12.

Figshare
Openalex Percentile: Top 78%
Fluorine in Organic Chemistry
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