Synlett 2016; 27(02): 304-308
DOI: 10.1055/s-0035-1560707
letter
© Georg Thieme Verlag Stuttgart · New York

An Azide-Functionalized Nitronyl Nitroxide Radical: Synthesis, Characterization and Staudinger–Bertozzi Ligation Reactivity

Stephanie M. Barbon
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
,
Pierangelo Gobbo
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
,
Wilson Luo
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
,
Jacquelyn T. Price
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
,
Mark C. Biesinger
b   Surface Science Western, The University of Western Ontario, 999 Collip Circle, London, ON, N6G 0J3, Canada
,
Mark S. Workentin*
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
,
Joe B. Gilroy*
a   Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research (CAMBR), The University of Western Ontario, 1151 Richmond St. N., London, ON, N6A 5B7, Canada   Email: mworkent@uwo.ca   joe.gilroy@uwo.ca
› Author Affiliations
Further Information

Publication History

Received: 31 July 2015

Accepted after revision: 15 September 2015

Publication Date:
14 October 2015 (online)


Abstract

An azide-functionalized nitronyl nitroxide was synthesized and its reactivity towards the Staudinger–Bertozzi ligation was explored. Whereas a model reaction in solution showed the conversion of nitronyl nitroxide to an imino nitroxide radical, the same reaction at the interface of gold nanoparticles allowed for successful covalent incorporation of the nitronyl nitroxide radical onto the nanoparticles.

Supporting Information

Primary Data

 
  • References and Notes

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