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Bissinger P, Braunschweig H, Damme A, et al. Isolation of a neutral boron-containing radical stabilized by a cyclic (alkyl)(amino)carbene. Angew Chem Int Ed Engl. 2014;53(28):7360-3doi: 10.1002/anie.201403514.
Bissinger, P., Braunschweig, H., Damme, A., Krummenacher, I., Phukan, A. K., Radacki, K., & Sugawara, S. (2014). Isolation of a neutral boron-containing radical stabilized by a cyclic (alkyl)(amino)carbene. Angewandte Chemie (International ed. in English), 53(28), 7360-3. https://doi.org/10.1002/anie.201403514
Bissinger, Philipp, et al. "Isolation of a neutral boron-containing radical stabilized by a cyclic (alkyl)(amino)carbene." Angewandte Chemie (International ed. in English) vol. 53,28 (2014): 7360-3. doi: https://doi.org/10.1002/anie.201403514
Bissinger P, Braunschweig H, Damme A, Krummenacher I, Phukan AK, Radacki K, Sugawara S. Isolation of a neutral boron-containing radical stabilized by a cyclic (alkyl)(amino)carbene. Angew Chem Int Ed Engl. 2014 Jul 07;53(28):7360-3. doi: 10.1002/anie.201403514. Epub 2014 Jun 10. PMID: 24917474.
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Angew Chem Int Ed Engl. 2014 Jul 07;53(28):7360-3. doi: 10.1002/anie.201403514. Epub 2014 Jun 10.

Isolation of a neutral boron-containing radical stabilized by a cyclic (alkyl)(amino)carbene.

Angewandte Chemie (International ed. in English)

Philipp Bissinger, Holger Braunschweig, Alexander Damme, Ivo Krummenacher, Ashwini K Phukan, Krzysztof Radacki, Shun Sugawara

Affiliations

  1. Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg (Germany).

PMID: 24917474 DOI: 10.1002/anie.201403514

Abstract

Utilizing a cyclic (alkyl)(amino)carbene (CAAC) as a ligand, neutral CAAC-stabilized radicals containing a boryl functionality could be prepared by reduction of the corresponding haloborane adducts. The radical species with a duryl substituent was fully characterized by single-crystal X-ray structural analysis, EPR spectroscopy, and DFT calculations. Compared to known neutral boryl radicals, the isolated radical species showed larger spin density on the boron atom. Furthermore, the compound that was isolated is extraordinarily stable to high temperatures under inert conditions, both in solution and in the solid state. Electrochemical investigations of the radical suggest the possibility to generate a stable formal boryl anion species.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: boron; carbenes; radicals; reduction; structure elucidation

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