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-economic method respects the principles of Green Chemistry. Furthermore, in each case this transformation shows an exclusive regioselectivity towards the anti-Markovnikov products.
Highlights
Phosphorus chemistry is prominent for its essential roles in the metabolism of phosphates in animals and plants
Using 2-methyltetrahydrofuran, the product was formed with 5% conversion. 2-Methyltetrahydrofuran offers many advantages with regards to the principles of Green Chemistry.[21,22,23]
We have shown that a large range of tertiary diphenylphosphine derivatives can be readily obtained in high yields by direct reaction of diphenylphosphine and alkene in presence of few equivalents of bio-mass derived 2-Me-THF
Summary
Phosphorus chemistry is prominent for its essential roles in the metabolism of phosphates in animals and plants. Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines† 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.
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