Photocatalytic Defluorinative\nα‑Aminoalkylation\nof Allylic Difluorides

A photocatalytic process was devised to synthesize monofluoroalkenes\nvia defluorinative functionalization of allylic difluorides. <i>N</i>-Alkylanilines are used as precursors to α-aminoalkyl\nradicals, which undergo regioselective addition to allylic difluorides,\nand subsequent SET and fluoride elimination produce monofluoroalkenes.\nC–C bond formation on the aniline is site-selective for the\nleast substituted carbon α to nitrogen.

Publication Details

Journal
Figshare
Published
2024-09-04
DOI
https://doi.org/10.1021/acs.joc.4c01861.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photocatalytic Defluorinative\nα‑Aminoalkylation\nof Allylic Difluorides

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Fluorine in Organic Chemistry
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Photocatalytic Defluorinative\nα‑Aminoalkylation\nof Allylic Difluorides

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Abstract

A photocatalytic process was devised to synthesize monofluoroalkenes\nvia defluorinative functionalization of allylic difluorides. <i>N</i>-Alkylanilines are used as precursors to α-aminoalkyl\nradicals, which undergo regioselective addition to allylic difluorides,\nand subsequent SET and fluoride elimination produce monofluoroalkenes.\nC–C bond formation on the aniline is site-selective for the\nleast substituted carbon α to nitrogen.

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Fluorine in Organic Chemistry
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Photocatalytic Defluorinative\nα‑Aminoalkylation\nof Allylic Difluorides · Figshare (2024) | TGRS Research Map | TGRS