Reaction of Tri(2-pyridyl)phosphine with Electron-Deficient Alkynes in Water: Stereoselective Synthesis of Functionalized Pyridylvinylphosphine Oxides
作者： Svetlana N. Arbuzova , Nina K. Gusarova , Tatyana E. Glotova , Igor A. Ushakov , Svetlana I. Verkhoturova
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摘要: The reaction of tri(2-pyridyl)phosphine with electron-deficient alkynes in water proceeds under mild conditions (40–45 °C, without catalyst, 4–5 h) liberation pyridine to give (E)-pyridylvinylphosphine oxides 45–56 % yields, the only exception being cyanophenylacetylene, which affords corresponding vinylphosphine oxide Z-configuration 40 % yield. is likely triggered by zwitterion, adduct electrophilic acetylenes, carbanionic center then neutralized a proton from water. intermediate phosphonium hydroxide finally decomposes product.
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