<i>N</i>-Directed Two-Fold Bromoboration of Diynes Enables Access to Brominated BN-Embedded PAHs
N-directed 2-fold bromoboration reactions of diynes with BBr3 have been developed, allowing the access to novel internally BN-doped polycyclic aromatic hydrocarbons from readily available precursors under mild conditions. Computational investigations identified three potential reaction mechanisms, each involving either BBr3 or [BBr4]−, with low activation barriers (ΔG‡ < 16 kcal/mol) for all pathways. The resulting brominated products can be further functionalized through various cross-coupling protocols, enabling the synthesis of highly luminescent emitters with quantum yield exceeding 90.
Authors
- Qin Ni (ORCID: https://orcid.org/0000-0002-1039-8927)
- Xiaoran Feng (ORCID: https://orcid.org/0000-0002-5645-5691)
- Kang Yuan (ORCID: https://orcid.org/0000-0002-9766-6815)
- Michael J. Ingleson (ORCID: https://orcid.org/0000-0001-9975-8302)
- Bing Wang (ORCID: https://orcid.org/0000-0003-0237-1107)
- Zhaobo Liu (ORCID: https://orcid.org/0000-0002-5882-4745)
Institutions
- Chinese Academy of Sciences (CN)
- Hainan University (CN)
- Ningbo Institute of Industrial Technology (CN)
- University of Edinburgh (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-21
- DOI
- https://doi.org/10.1021/acs.orglett.4c03952
- Citations
- 6
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- National Natural Science Foundation of China
- Beijing Institute of Technology
- Engineering and Physical Sciences Research Council