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Issue 24, 2013
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Boron azides in Staudinger oxidations and cycloadditions

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Staudinger reactions of Cy2BN3 with tri-substituted phosphines (R3P) yielded the boron–nitrogen–phosphorus linked systems Cy2BN[double bond, length as m-dash]PR3 (R = Et, tBu, Cy, Ph) (1a–1d respectively). Similarly, reaction of (C6F5)2BN3 with the phosphines PtBu3, PPh3, Ph2PC[triple bond, length as m-dash]CPh and Ph2PC[triple bond, length as m-dash]CPPh2 yielded (C6F5)2BN[double bond, length as m-dash]PR3 (2a–d respectively). In contrast, the reaction of (C6F5)2BN3 with Ph2P–C[triple bond, length as m-dash]Cp-tol in the presence of excess Me3SiN3 afforded the bicyclic product 3 [1-(C6F5)2B-4-(p-tol)-1H-1,2,3-triazole-5-P(NH)Ph2] in which both a Staudinger and a cycloaddition reaction has taken place. However, if the Staudinger reaction is prohibited via phosphine oxidation as in the case of (EtO)2P(O)C[triple bond, length as m-dash]CP(O)(OEt)2 then the unusual dimeric product 4 [2-(C6F5)2B-4-(P(O)OEt2)-2H-1,2,3-triazole-5-P(O)(OEt)(OB(C6F5)2)] is generated. The structures of 1b–d, 2b–d, 3 and 4 have been determined by X-ray diffraction.

Graphical abstract: Boron azides in Staudinger oxidations and cycloadditions

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The article was received on 24 Mar 2013, accepted on 23 Apr 2013 and first published on 24 Apr 2013

Article type: Paper
DOI: 10.1039/C3DT50791B
Citation: Dalton Trans., 2013,42, 8674-8683

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    Boron azides in Staudinger oxidations and cycloadditions

    R. L. Melen, A. J. Lough and D. W. Stephan, Dalton Trans., 2013, 42, 8674
    DOI: 10.1039/C3DT50791B

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