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Ohsato T, Okuno Y, Ishida S, et al. A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene. Angew Chem Int Ed Engl. 2016;55(38):11426-30doi: 10.1002/anie.201605005.
Ohsato, T., Okuno, Y., Ishida, S., Iwamoto, T., Lee, K. H., Lin, Z., Yamashita, M., & Nozaki, K. (2016). A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene. Angewandte Chemie (International ed. in English), 55(38), 11426-30. https://doi.org/10.1002/anie.201605005
Ohsato, Takuto, et al. "A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene." Angewandte Chemie (International ed. in English) vol. 55,38 (2016): 11426-30. doi: https://doi.org/10.1002/anie.201605005
Ohsato T, Okuno Y, Ishida S, Iwamoto T, Lee KH, Lin Z, Yamashita M, Nozaki K. A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene. Angew Chem Int Ed Engl. 2016 Sep 12;55(38):11426-30. doi: 10.1002/anie.201605005. Epub 2016 Aug 17. PMID: 27533099.
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Angew Chem Int Ed Engl. 2016 Sep 12;55(38):11426-30. doi: 10.1002/anie.201605005. Epub 2016 Aug 17.

A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene.

Angewandte Chemie (International ed. in English)

Takuto Ohsato, Yuri Okuno, Shintaro Ishida, Takeaki Iwamoto, Ka-Ho Lee, Zhenyang Lin, Makoto Yamashita, Kyoko Nozaki

Affiliations

  1. Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551, Tokyo, Japan.
  2. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656, Tokyo, Japan.
  3. Department of Chemistry, Graduate School of Science, Tohoku University, 980-8578, Sendai, Japan.
  4. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong.
  5. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong. [email protected].
  6. Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551, Tokyo, Japan. [email protected].
  7. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656, Tokyo, Japan. [email protected].

PMID: 27533099 DOI: 10.1002/anie.201605005

Abstract

A potassium diboryllithate (B2 LiK) was synthesized and structurally characterized. DFT calculations, including NPA and AIM analyses of B2 LiK, revealed ionic interactions between the two bridging boryl anions and Li(+) and K(+) . Upon standing in benzene, B2 LiK deprotonated the solvent to form a hydroborane and a phenylborane. On the basis of DFT calculations, a detailed reaction mechanism, involving deprotonation and hydride/phenyl exchange processes, is proposed. An NBO analysis of the transition state for the deprotonation of benzene suggests that the deprotonation should be induced by the coordination of benzene to the K(+) .

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: benzene; boron; computational chemistry; structure determination; superbases

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