Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines - Archive ouverte HAL Access content directly
Journal Articles RSC Advances Year : 2019

Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines

Abstract

A hydrophosphination reaction that is free of base, acid and catalyst, using only 2-methyltetrahydrofuran as additive has been performed. A new family of mono-, di,-tri-and tetra-phosphines compounds are obtained in good to excellent yields by adding diphenylphosphine to alkenes, mono-and polyfunctional acrylics (based on acrylate and methacrylate motifs) and acrylamide substrates. Addition of four equivalent of bio-mass derived 2-MeTHF into the reaction media improves both conversion and time of the reaction and reduces the sensitivity of the reactants over oxidation. This simple, straightforward and atom-economy method respects the principles of Green Chemistry. Furthermore, in each case this transformation shows an exclusive regioselectivity towards the anti-Markovnikov products.
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Dates and versions

hal-02330387 , version 1 (23-10-2019)

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Damien Bissessar, Julien Egly, Thierry Achard, Pascal Steffanut, Stéphane Bellemin-Laponnaz. Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines. RSC Advances, 2019, 9 (47), pp.27250-27256. ⟨10.1039/C9RA04896K⟩. ⟨hal-02330387⟩
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