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Isolation of a Neutral Boron‐Containing Radical Stabilized by a Cyclic (Alkyl)(Amino)Carbene
Author(s) -
Bissinger Philipp,
Braunschweig Holger,
Damme Alexander,
Krummenacher Ivo,
Phukan Ashwini K.,
Radacki Krzysztof,
Sugawara Shun
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403514
Subject(s) - carbene , chemistry , radical , substituent , alkyl , adduct , boron , electron paramagnetic resonance , medicinal chemistry , photochemistry , crystallography , polymer chemistry , organic chemistry , physics , nuclear magnetic resonance , catalysis
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.