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New Blatter-type radicals from a bench-stable carbene

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

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


Jacob A. Grant

Zhou Lu

David E. Tucker

Bryony M. Hockin

Dmitry S. Yufit

Victor Chechik


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.


Grant, J. A., Lu, Z., Tucker, D. E., Hockin, B. M., Yufit, D. S., Fox, M. A., …O'Donoghue, A. C. (2017). New Blatter-type radicals from a bench-stable carbene. Nature Communications, 8, Article 15088.

Journal Article Type Article
Acceptance Date Feb 28, 2017
Online Publication Date May 15, 2017
Publication Date May 15, 2017
Deposit Date Feb 6, 2017
Publicly Available Date May 16, 2017
Journal Nature Communications
Publisher Nature Research
Peer Reviewed Peer Reviewed
Volume 8
Article Number 15088
Public URL


Published Journal Article (558 Kb)

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