A Remarkable Catalyst-Free Photochemical Alkene Hydrophosphination with Bis(trimethylsilyl)phosphonite
Name
a-remarkable-catalyst-free-photochemical-alkene-hydrophosphination-with-bis(trimethylsilyl)phosphonite.pdf
Description
Published version
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2.83 MB
Format
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Checksum (MD5)
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Author(s)
Bréger, Eloïse
Dussart-Gautheret, Jade
Taakili, Rachid
Fontaine-Vive, Fabien
Cummins, Christopher C
Benhida, Rachid
Date Issued
June 3, 2025
Journal
JACS Au
Publisher
American Chemical Society
Citation
A Remarkable Catalyst-Free Photochemical Alkene Hydrophosphination with Bis(trimethylsilyl)phosphonite. Eloïse Bréger, Jade Dussart-Gautheret, Rachid Taakili, Fabien Fontaine-Vive, Christopher C. Cummins, and Rachid Benhida. JACS Au 2025 5 (6), 2861-2870.
Version
Final published version
Abstract
This publication delves into a comprehensive exploration of a new synthetic route to functionalized phosphorus-derived compounds. Bis(trimethylsilyl)phosphonite HP(OSiMe3)2, prepared in a high yield from H3PO2, was found to be an excellent reagent for hydrophosphination of activated, unactivated, and amino acid-derived olefins under UV irradiation and catalyst-, solvent- and glovebox-free conditions. The resulting phosphorus trivalent compounds have been subjected to postfunctionalization, leading to the formation of H-phosphinate, phosphonate, and thiophosphonate end products in good to excellent yields. With a combination of experimental and theoretical calculations, the mechanism for this hydrophosphination reaction has been investigated, revealing a radical process.
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DOI of Published Version
https://doi.org/10.1021/jacsau.5c00444
