Work

N-Directed Two-Fold Bromoboration of Diynes Enables Access to Brominated BN-Embedded PAHs

Year: 2024

Type: article

Abstract: N -directed 2-fold bromoboration reactions of diynes with BBr 3 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 BBr 3 or [BBr 4 ] −, 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03952

Authors: Xiaoran Feng, Zhaobo Liu, Qing-Yun Ni, Bing Wang, Michael J. Ingleson, Kang Yuan

Institutions: Chinese Academy of Sciences, Ningbo Institute of Industrial Technology, University of Edinburgh, Hainan University

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Natural Science Foundation of China, Beijing Institute of Technology, Engineering and Physical Sciences Research Council

Awards: G1669157076, G1981394742, G2110651246, G4861520817, Boron: Beyond the Reagent