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Interception of intermediates in phosphine oxidation by mesityl nitrile-N-oxide using frustrated Lewis pairs

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Abstract

Phosphine oxidation by MesCNO is rapid; however, an FLP strategy intercepts the 1,3 addition products including [MesC(R3P)NOB(C6F5)3] (R = Ph 1, p-tol 2), [MesC(Mes2PH)NOB(C6F5)3] 3 (MesC(NOB(C6F5)3)Ph2P)2(CH2)n (n = 2: 4, 3: 5) and [MesC(Ph3P)NOB(C6F4H)3] 6. These species are shown to react with tBuOK or [Bu4N]F permitting the oxidation to proceed via a process involving borane dissociation. Similarly, the equilibrium established by 1 with B(C6F4H)3 and 6 with B(C6F5)3 provides experimental support for the “Cummins mechanism” for these phosphine oxidations.

Graphical abstract: Interception of intermediates in phosphine oxidation by mesityl nitrile-N-oxide using frustrated Lewis pairs

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Publication details

The article was received on 30 Apr 2018, accepted on 05 Jun 2018 and first published on 06 Jun 2018


Article type: Paper
DOI: 10.1039/C8DT01717D
Citation: Dalton Trans., 2018, Advance Article
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    Interception of intermediates in phosphine oxidation by mesityl nitrile-N-oxide using frustrated Lewis pairs

    K. M. Szkop, D. Zhu, L. E. Longobardi, J. Heck and D. W. Stephan, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT01717D

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