Formation of an air-stable diborane via a stepwise BH3 addition of pyrido[1,2-a]isoindole with H2 evolution

Jiaqi Dong; Lutao Zhang; Dehui Tan; Jianfeng Wu; Nan Wang; Soren K. Mellerup; Suning Wang; Deng-Tao Yang

doi:10.1039/D1CC04228A

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Formation of an air-stable diborane via a stepwise BH₃ addition of pyrido[1,2-a]isoindole with H₂ evolution†

Jiaqi Dong,‡^a Lutao Zhang,

‡^a Dehui Tan,^a Jianfeng Wu,^a Nan Wang,

*^b Soren K. Mellerup,^c Suning Wang

^c and Deng-Tao Yang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, China
E-mail: dtyang@nwpu.edu.cn

^b Key Laboratory of Cluster Science, Ministry of Education of China, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering Beijing Institute of Technology, Beijing, China
E-mail: nanwang@bit.edu.cn

^c Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada

Abstract

A novel and air-stable organo(hydro)diborane featuring a five-membered aryl ring supported bridging B–C–B three-centre–two-electron (3c–2e) bond has been reported. Pyrido[1,2-a]isoindole was found to undergo a stepwise BH₃ addition reaction, during which a mono-BH₃ adduct was formed from a electrophilic addition at the C^γ in pyrido[1,2-a]isoindole. A molecule of hydrogen was eliminated throughout the second step of addition reaction. DFT calculations indicate that the H₂ evolution is concerted to the second BH₃ addition rather than forming B [double bond, length as m-dash] C before the second BH₃ attack.

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Article information

DOI: https://doi.org/10.1039/D1CC04228A
Article type: Communication
Submitted: 03 Aug 2021
Accepted: 02 Sep 2021
First published: 02 Sep 2021

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Chem. Commun., 2021,57, 9882-9885

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Formation of an air-stable diborane via a stepwise BH₃ addition of pyrido[1,2-a]isoindole with H₂ evolution

J. Dong, L. Zhang, D. Tan, J. Wu, N. Wang, S. K. Mellerup, S. Wang and D. Yang, Chem. Commun., 2021, 57, 9882 DOI: 10.1039/D1CC04228A

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