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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605005
Subject(s) - deprotonation , chemistry , benzene , natural bond orbital , ionic bonding , medicinal chemistry , computational 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 + .