Isolable diboryl radicals acting as highly efficient reaction intermediates under mild conditions

Rui Feng; Wenbang Yang; Wenqing Wang; Yue Zhao; Gengwen Tan; Li Zhang; Xinping Wang

doi:10.1039/C9CC06514H

Isolable diboryl radicals acting as highly efficient reaction intermediates under mild conditions†

Rui Feng,‡^a Wenbang Yang,‡^a Wenqing Wang,^ab Yue Zhao,

^a Gengwen Tan,

*^a Li Zhang*^ac and Xinping Wang

*^a

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* Corresponding authors

^a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
E-mail: gengwentan@nju.edu.cn, xpwang@nju.edu.cn, 544601409@qq.com

^b College of Chemistry and Materials Science, Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Anhui Normal University, Wuhu, Anhui 241002, China

^c Center of Materials Science and Engineering, Guangxi University of Science and Technology, Liuzhou 545006, China

Abstract

Activation of the B–B bond in diborane B₂(OR)₄ with dimesitylpyridylboranes 1 and 2 afforded stable diboryl radicals 3 and 4 in moderate yields, respectively, which were studied by single crystal X-ray crystallography, EPR and UV/Vis spectroscopy, in conjunction with theoretical calculations. The diboryl radicals could react with the substrates p-benzoquinone, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and its derivative to form useful boron-containing reagents. Moreover, a much higher yield was achieved in the catalytic reaction of p-benzoquinone and diborane with 1 or 2 in comparison to 4-cyanopyridine as the catalyst, in which the diboryl radicals act as reaction intermediates, highlighting the importance of the stability of the boryl radicals in improving the reaction efficiency.

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DOI: https://doi.org/10.1039/C9CC06514H
Article type: Communication
Submitted: 22 Aug 2019
Accepted: 18 Sep 2019
First published: 18 Sep 2019

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Chem. Commun., 2019,55, 12908-12911

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Isolable diboryl radicals acting as highly efficient reaction intermediates under mild conditions

R. Feng, W. Yang, W. Wang, Y. Zhao, G. Tan, L. Zhang and X. Wang, Chem. Commun., 2019, 55, 12908 DOI: 10.1039/C9CC06514H

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Isolable diboryl radicals acting as highly efficient reaction intermediates under mild conditions†

Abstract

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Isolable diboryl radicals acting as highly efficient reaction intermediates under mild conditions

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