C–C bond-forming reactions of 2-isocyanobiphenyl·BX<sub>3</sub> adducts: spontaneous construction of polycyclic heteroaromatics
The syntheses and reactivities of 2-isocyanobiphenyl·BX<sub>3</sub> 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 <i>via</i> a competing pathway. Mechanistic details are probed experimentally and computationally.
Authors
- Yu-Tsen Kuo
- Yi‐Hung Liu (ORCID: https://orcid.org/0000-0002-0800-7421)
- Jeffrey M. Farrell (ORCID: https://orcid.org/0000-0001-5377-354X)
- Mu‐Jeng Cheng (ORCID: https://orcid.org/0000-0002-8121-0485)
- Chao Yao
Institutions
- National Taiwan University (TW)
- National Cheng Kung University (TW)
Publication Details
- Journal
- Dalton Transactions
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5dt00210a
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Ministry of Education