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Issue 46, 2018
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Long sought synthesis of quaternary phosphonium salts from phosphine oxides: inverse reactivity approach

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Abstract

Quaternary phosphonium salts (QPS), a key class of organophosphorus compounds, have previously only been available by routes involving nucleophilic phosphorus. We report the realisation of the opposite approach to QPS utilising phosphine oxides as the electrophilic partner and Grignard reagents as nucleophiles. The process is enabled through the crucial intermediacy of the derived halophosphonium salts. The route does not suffer from the slow kinetics and limited availability of many parent phosphines and a broad range of QPS were prepared in excellent yields.

Graphical abstract: Long sought synthesis of quaternary phosphonium salts from phosphine oxides: inverse reactivity approach

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Publication details

The article was received on 20 Mar 2018, accepted on 24 Apr 2018 and first published on 01 May 2018


Article type: Communication
DOI: 10.1039/C8CC02173B
Chem. Commun., 2018,54, 5843-5846

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    Long sought synthesis of quaternary phosphonium salts from phosphine oxides: inverse reactivity approach

    A. C. Vetter, K. Nikitin and D. G. Gilheany, Chem. Commun., 2018, 54, 5843
    DOI: 10.1039/C8CC02173B

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