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A Zwitterionic Carbanion Frustrated by Boranes – Dihydrogen Cleavage with Weak Lewis Acids via an “Inverse” Frustrated Lewis Pair Approach
- Li, Hui, Aquino, Adelia J. A., Cordes, David B., Hung-Low, Fernando, Hase, William L., Krempner, Clemens
- Journal of the American Chemical Society 2013 v.135 no.43 pp. 16066-16069
- Lewis acids, boranes, borates, chemistry, hydrogen, sodium, zwitterions
- The synthesis, structural characterization, and acid–base chemistry of [C(SiMe₂OCH₂CH₂OMe)₃]Na (2), a sterically encumbered zwitterionic organosodium compound, is reported. 2 is a strong Brønsted base that forms frustrated Lewis pairs (FLPs) with a number of boron-containing Lewis acids ranging from weakly Lewis acidic aryl and alkyl boranes to various alkyl borates. These intermolecular FLPs readily cleave H₂, which confirms that even poor Lewis acids can engage in FLP-mediated H₂ cleavage provided that the present bulky base is of sufficiently high Brønsted basicity.