C–C bond-forming reactions of 2-isocyanobiphenyl·BX3 adducts: spontaneous construction of polycyclic heteroaromatics

Yu-Tsen Kuo; Chia-Yu Yao; Yi-Hung Liu; Mu-Jeng Cheng; Jeffrey M. Farrell

doi:10.1039/D5DT00210A

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C–C bond-forming reactions of 2-isocyanobiphenyl·BX₃ adducts: spontaneous construction of polycyclic heteroaromatics†

Yu-Tsen Kuo,

^a Chia-Yu Yao,^b Yi-Hung Liu,^a Mu-Jeng Cheng

^b and Jeffrey M. Farrell

*^ac

Author affiliations

* Corresponding authors

^a Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan
E-mail: farrell@ntu.edu.tw

^b Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan

^c Center for Emerging Materials and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan

Abstract

The syntheses and reactivities of 2-isocyanobiphenyl·BX₃ adducts (X = I, Br, Cl) are reported. These adducts undergo unexpected C–H bond-functionalizing cyclization upon heating, yielding phenanthridinium-6-trihaloborate zwitterions. Where X = Cl, an unexpected helical polycyclic boronium salt is formed via a competing pathway. Mechanistic details are probed experimentally and computationally.

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Article information

DOI: https://doi.org/10.1039/D5DT00210A
Article type: Communication
Submitted: 25 Jan 2025
Accepted: 14 Mar 2025
First published: 19 Mar 2025

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Dalton Trans., 2025,54, 7189-7193

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C–C bond-forming reactions of 2-isocyanobiphenyl·BX₃ adducts: spontaneous construction of polycyclic heteroaromatics

Y. Kuo, C. Yao, Y. Liu, M. Cheng and J. M. Farrell, Dalton Trans., 2025, 54, 7189 DOI: 10.1039/D5DT00210A

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