Tributylphosphine catalyzed addition of diphenylphosphine oxide to unsubstituted and substituted electron-deficient alkenes

Abstract

© 2018 Elsevier Ltd The PBu3-catalyzed conjugate addition of diphenylphosphine oxide to unsubstituted and substituted electron-deficient alkenes is reported. β-Substituted α,β-unsaturated esters, trans-methyl crotonate and trans-methyl cinnamate, known for their reluctance to participate in phosphine-catalyzed transformations, also react well under the developed conditions. Mild reaction conditions, simple work-up and the ease of catalyst recovery make the proposed methodology useful for the preparation of functionalized tertiary phosphine oxides. The utility of this method was demonstrated by the gram-scale reactions of diphenylphosphine oxide with electron-deficient alkenes.