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Issue 11, 2012
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Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes

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Abstract

Diazo compounds, which can be accessed directly from azides by deimidogenation, are shown to be extremely versatile dipoles in 1,3-dipolar cycloaddition reactions with a cyclooctyne. The reactivity of a diazo compound can be much greater or much less than its azide analog, and is enhanced markedly in polar-protic solvents. These reactivities are predictable from frontier molecular orbital energies. The most reactive diazo compound exhibited the highest known second-order rate constant to date for a dipolar cycloaddition with a cycloalkyne. These data provide a new modality for effecting chemoselective reactions in a biological context.

Graphical abstract: Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes

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Publication details

The article was received on 24 Jun 2012, accepted on 02 Aug 2012 and first published on 02 Aug 2012


Article type: Edge Article
DOI: 10.1039/C2SC20806G
Citation: Chem. Sci., 2012,3, 3237-3240
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    Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes

    N. A. McGrath and R. T. Raines, Chem. Sci., 2012, 3, 3237
    DOI: 10.1039/C2SC20806G

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