Jump to main content
Jump to site search

Issue 24, 2013
Previous Article Next Article

Boron azides in Staudinger oxidations and cycloadditions

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Publication details

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
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements