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Stable Boron Dithiolene Radicals
Author(s) -
Wang Yuzhong,
Xie Yaoming,
Wei Pingrong,
Blair Soshawn A.,
Cui Dongtao,
Johnson Michael K.,
Schaefer Henry F.,
Robinson Gregory H.
Publication year - 2018
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.201804298
Subject(s) - radical , boron , photochemistry , chemistry , materials science , organic chemistry
Whereas low‐temperature (−78 °C) reaction of the lithium dithiolene radical 1 . with boron bromide gives the dibromoboron dithiolene radical 2 . , the parallel reaction of 1 . with (C 6 H 11 ) 2 BCl (0 °C) affords the dicyclohexylboron dithiolene radical 3 . . Radicals 2 . and 3 . were characterized by single‐crystal X‐ray diffraction, UV/Vis, and EPR spectroscopy. The nature of these radicals was also probed computationally. Under mild conditions, 3 . undergoes unexpected thiourea‐mediated B−C bond activation to give zwitterion 4 , which may be regarded as an anionic dithiolene‐modified carbene complex of the sulfenyl cation RS + (R=cyclohexyl).