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

RSC Adv

Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg, CNRS UMR 7504 23 Rue du Loess, BP 43 F-67034 Strasbourg Cedex 2 France

Published: August 2019

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070578PMC
http://dx.doi.org/10.1039/c9ra04896kDOI Listing

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