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Issue 12, 2013
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Cu(i)-catalysed N–H insertion in water: a new tool for chemical biology

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Abstract

We demonstrate for the first time that Cu(I)-catalysis can deliver N–H insertion (NHI) with α-diazocarbonyl compounds in aqueous media. Despite being carried out in water only trace amounts of O–H insertion are seen, indicating the catalyst's overwhelming preference for NHI. Our optimized conditions for NHI converged with those used for the Cu-catalyzed azide–alkyne cycloaddition (CuAAC) for bioconjugation, spurring us to develop an auto-tandem catalytic process where both catalytic cycles operate simultaneously in one-pot. We explore the scope of the method with both small molecule and complex DNA and RNA substrates.

Graphical abstract: Cu(i)-catalysed N–H insertion in water: a new tool for chemical biology

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Publication details

The article was received on 15 May 2013, accepted on 22 Aug 2013 and first published on 16 Sep 2013


Article type: Edge Article
DOI: 10.1039/C3SC51363G
Chem. Sci., 2013,4, 4401-4406

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    Cu(I)-catalysed N–H insertion in water: a new tool for chemical biology

    K. Tishinov, N. Fei and D. Gillingham, Chem. Sci., 2013, 4, 4401
    DOI: 10.1039/C3SC51363G

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