Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 28, Pages 7360-7363Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403514
Keywords
boron; carbenes; radicals; reduction; structure elucidation
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Funding
- German Science Foundation (DFG)
- Fonds der chemischen Industrie (FCI)
- JSPS Fellowship for Young Scientists
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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.
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