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Dai, Wen; Geib, Steven J; Curran, Dennis P
Journal of the American Chemical Society, 02/2019, Letnik: 141, Številka: 8Journal Article
The first ring-opening reactions of ligated boriranes (boracyclopropanes) are described. Treatment of readily available NHC-boriranes bearing ester substituents on the borirane ring with HCl provides stable γ-NHC-bora-γ-lactones in isolated yields ranging from 40% to 73%. The reactions occur through 1,3-addition of HCl across a B–C bond of the NHC-borirane to form a ring-opened NHC-boryl chloride, followed by lactonization with chloride displacement. Experimental evidence suggests that both the borirane ring-opening reaction and the boralactonization reaction occur with inversion at boron.
