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31.40.1.1.7.7 Variation 7: Arylphosphinic Esters by Hydrophosphination of Alkynes

DOI: 10.1055/sos-SD-031-02233

Cristau, H.-J.; Virieux, D.Science of Synthesis, (2007311998.

Hydrophosphination of alkynes in the presence of a palladium or nickel catalyst affords vinylphosphinates 94 or 95 in good yields (Scheme 70).[‌237‌‌239‌] Interestingly, when monosubstituted alkynes are used, the regioselectivity of the reaction can be easily controlled by the presence of small amounts of diphenylphosphinic acid. The synthesis of enantiomerically pure O-menthyl alkenyl(phenyl)phosphinates 96 by palladium-catalyzed hydrophosphinylation of alkynes occurs stereospecifically with retention of configuration at the phosphorus atom.[‌239‌]

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