Synthesis of Boriranes by Double Hydroboration Reactions of N-Heterocyclic Carbene Boranes and Dimethyl Acetylenedicarboxylate

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• 作者：Timothy R. McFadden ; Cheng Fang ; Steven J. Geib ; Everett Merling ; Peng LiuDennis P. Curran
• 刊名：Journal of the American Chemical Society
• 出版年：2017
• 出版时间：February 8, 2017
• 年：2017
• 卷：139
• 期：5
• 页码：1726-1729
• 全文大小：355K
• ISSN：1520-5126

文摘

Reaction of bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene borane with dimethyl acetylenedicarboxylate gives 80% yield of a stable borirane (boracyclopropane) formed by formal double hydroboration along with 5% of the (E)-alkenylborane. DFT calculations suggest a mechanism where divergence to the two products occurs after a common initial stage of hydride transfer from the NHC-borane to the acetylenedicarboxylate.