Stable Boron Dithiolene Radicals. (22nd May 2018)

• Record Type: Journal Article
• Authors: Wang, Yuzhong; Xie, Yaoming; Wei, Pingrong; Blair, Soshawn A.; Cui, Dongtao; Johnson, Michael K.; Schaefer, Henry F.; Robinson, Gregory H.
• Is Part Of: Angewandte Chemie. Volume 130:Number 26(2018)
• Page Start: 7991
• Page End: 7994
• Publication Date: 2018-05-22
• Subjects: B-C-Aktivierung -- Bor -- Carbene -- Dithiolene -- Radikale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804298
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Whereas low‐temperature (−78 °C) reaction of the lithium dithiolene radical1 . with boron bromide gives the dibromoboron dithiolene radical2 ., the parallel reaction of1 . with (C6 H11 )2 BCl (0 °C) affords the dicyclohexylboron dithiolene radical3 . . Radicals2 . and3 . 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 zwitterion4, which may be regarded as an anionic dithiolene‐modified carbene complex of the sulfenyl cation RS + (R=cyclohexyl).