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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7189-7193
Number of pages	5
Journal	Dalton Transactions
Volume	54
Issue number	18
DOIs	https://doi.org/10.1039/d5dt00210a
Publication status	Published - 2025 Mar 19

All Science Journal Classification (ASJC) codes

Inorganic Chemistry

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10.1039/d5dt00210a

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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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AU - Kuo, Yu Tsen

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AU - Liu, Yi Hung

AU - Cheng, Mu Jeng

AU - Farrell, Jeffrey M.

PY - 2025/3/19

Y1 - 2025/3/19

N2 - 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.

AB - 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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ER -

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

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