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A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene
Author(s) -
Ohsato Takuto,
Okuno Yuri,
Ishida Shintaro,
Iwamoto Takeaki,
Lee KaHo,
Lin Zhenyang,
Yamashita Makoto,
Nozaki Kyoko
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605005
Subject(s) - deprotonation , chemistry , benzene , natural bond orbital , ionic bonding , computational chemistry , medicinal chemistry , inorganic chemistry , density functional theory , organic chemistry , ion
A potassium diboryllithate (B 2 LiK) was synthesized and structurally characterized. DFT calculations, including NPA and AIM analyses of B 2 LiK, revealed ionic interactions between the two bridging boryl anions and Li + and K + . Upon standing in benzene, B 2 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 + .