A Zwitterionic Carbanion Frustrated by Boranes - Dihydrogen Cleavage with Weak Lewis Acids via an %26quot;Inverse%26quot; Frustrated Lewis Pair Approach

作者:Li Hui; Aquino Adelia J A; Cordes David B; Hung Low Fernando; Hase William L; Krempner Clemens*
来源:Journal of the American Chemical Society, 2013, 135(43): 16066-16069.
DOI:10.1021/ja409330h

摘要

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 Bronsted 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 H-2, which confirms that even poor Lewis acids can engage in FLP-mediated H-2 cleavage provided that the present bulky base is of sufficiently high Bronsted basicity.

  • 出版日期2013-10-30