Paper
RSC Advances
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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. The presence of 2-
MeTHF into the reaction media improves both conversion and
time of the reaction and reduces the sensitivity of the reactants
over oxidation. This procedure is applicable to styrene deriva-
tives, a,b-unsaturated esters and amides and the corresponding
products were all formed with anti-Markovnikov regiose-
lectivity. Moreover, the easy availability of acrylic monomers
allowed us to synthesize a wide range of polyphosphines that
may of interest to the industry. It allowed us access to di-, tri-
and tetra-phosphines with good to excellent isolated yields in all
cases. This simple, straightforward and atom-economy method
follows the principles of Green Chemistry.
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General experimental procedure
General hydrophosphination procedure
All phosphines were prepared in 0.5 g to 10 g scale by addition
of the corresponding alkene compounds on diphenylphosphine
(PPh2H) in presence of 2-MeTHF (4 equiv.) under argon in
a closed vessel. The mixture was degassed under vacuum three
times then the stirred during 4 to 12 h at 90 ꢀC under argon in
a closed vessel. Hydrophosphination products were then puri-
ed by ash chromatography on silica gel (gradient from
cyclohexane to cyclohexane/ethyl acetate 8 : 2) (for more details
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Conflicts of interest
The authors declare that they have led a provisional patent
application.
Acknowledgements
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Financial support for this project was provided by the Region 12 (a) S. A. Pullarkat, Synthesis, 2016, 48, 493–503; (b)
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