Peer-Reviewed Journal Details
Mandatory Fields
Heaney, F
2012
June
European Journal of Organic Chemistry
Nitrile Oxide/Alkyne Cycloadditions - A Credible Platform for Synthesis of Bioinspired Molecules by Metal-Free Molecular Clicking
Published
83 ()
Optional Fields
COPPER-FREE CLICK RUTHENIUM-CATALYZED CYCLOADDITION AZIDE-ALKYNE CYCLOADDITION SOLID-PHASE SYNTHESIS HETEROCYCLIC NUCLEOSIDE ANALOGS 1,3-DIPOLAR CYCLOADDITION ONE-POT COPPER(I)-CATALYZED SYNTHESIS EFFICIENT SYNTHESIS LIVING SYSTEMS
3043
3058
The need for precise and flexible synthetic methodology to underpin modern research in chemical biology and materials science has fuelled a resurgence of interest in Huisgen 1,3-dipolar cycloaddition chemistry. Of late, the in vogue chemistry for the assembly of complex biological molecules and specialist materials has been the copper-catalysed azide alkyne cycloaddition (CuAAC) reaction. However, in certain circumstances aversion to the copper catalyst flaws this approach and alternatives have been sought. Click chemistry has developed beyond the original triazole-forming trick and azides are no longer the only dipoles pursued as click cycloaddition partners. This article reviews some of the complications of the CuAAC reaction and evaluates the potential of nitrile oxide/alkyne cycloaddition (NOAC) as a covalent conjugation tool. With a focus on applications in nucleic acid chemistry and materials science it presents the case for a prominent position for nitrile oxides in the catalyst-free bioconjugation toolbox.
WEINHEIM
1434-193X
10.1002/ejoc.201101823
Grant Details