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Grant JA, Lu Z, Tucker DE, et al. New Blatter-type radicals from a bench-stable carbene. Nat Commun. 2017;8:15088doi: 10.1038/ncomms15088.
Grant, J. A., Lu, Z., Tucker, D. E., Hockin, B. M., Yufit, D. S., Fox, M. A., Kataky, R., Chechik, V., & O'Donoghue, A. C. (2017). New Blatter-type radicals from a bench-stable carbene. Nature communications, 815088. https://doi.org/10.1038/ncomms15088
Grant, Jacob A, et al. "New Blatter-type radicals from a bench-stable carbene." Nature communications vol. 8 (2017): 15088. doi: https://doi.org/10.1038/ncomms15088
Grant JA, Lu Z, Tucker DE, Hockin BM, Yufit DS, Fox MA, Kataky R, Chechik V, O'Donoghue AC. New Blatter-type radicals from a bench-stable carbene. Nat Commun. 2017 May 15;8:15088. doi: 10.1038/ncomms15088. PMID: 28504260; PMCID: PMC5440670.
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Nat Commun. 2017 May 15;8:15088. doi: 10.1038/ncomms15088.

New Blatter-type radicals from a bench-stable carbene.

Nature communications

Jacob A Grant, Zhou Lu, David E Tucker, Bryony M Hockin, Dmitry S Yufit, Mark A Fox, Ritu Kataky, Victor Chechik, AnnMarie C O'Donoghue

Affiliations

  1. Department of Chemistry, Durham University, South Road, Durham DH1 3LE, UK.
  2. Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.

PMID: 28504260 PMCID: PMC5440670 DOI: 10.1038/ncomms15088

Abstract

Stable benzotriazinyl radicals (Blatter's radicals) recently attracted considerable interest as building blocks for functional materials. The existing strategies to derivatize Blatter's radicals are limited, however, and synthetic routes are complex. Here, we report that an inexpensive, commercially available, analytical reagent Nitron undergoes a previously unrecognized transformation in wet acetonitrile in the presence of air to yield a new Blatter-type radical with an amide group replacing a phenyl at the C(3)-position. This one-pot reaction of Nitron provides access to a range of previously inaccessible triazinyl radicals with excellent benchtop stabilities. Mechanistic investigation suggests that the reaction starts with a hydrolytic cleavage of the triazole ring followed by oxidative cyclization. Several derivatives of Nitron were prepared and converted into Blatter-type radicals to test the synthetic value of the new reaction. These results significantly expand the scope of using functionalized benzotriazinyls as stable radical building blocks.

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