Phosphenium-Cation-Mediated Formal Cycloaddition Approach to Benzophospholes

Chemistry : a European Journal
Kazutoshi NishimuraMasahiro Miura

Abstract

A phosphenium-cation-mediated formal [3+2]-cycloaddition reaction of internal alkynes is reported. The reaction proceeds under metal-free conditions to give the corresponding C-P rearranged benzophospholes regioselectively, even when ortho- and para-substituted arylphosphine oxides are starting substrates. Mechanistic studies by 31 P{1 H} NMR analysis suggest an involvement of three-membered phosphirenium cation species and C-P rearrangement prior to a ring closure for benzophosphole skeleton formation.

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Citations

Nov 21, 2018·Chemical Communications : Chem Comm·Atsushi UenoGerhard Erker
Oct 30, 2020·The Journal of Organic Chemistry·Zhantao YangJunbiao Chang

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