Visible-Light-Promoted [5 + 1] Annulation Initiated by Electron-Donor–Acceptor Complexes: Synthesis of Perfluoroalkyl‑s‑Triazines

A visible-light-promoted electron-donor–acceptor (EDA) complex-initiated [5 + 1] annulation between biguanides and perfluoroalkyl halides for the construction of perfluoroalkyl-s-triazines has been developed. It was found that both visible light and dioxygen in the air are favorable for the reaction...

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Bibliographic Details
Published in:Organic letters 2019-05, Vol.21 (9), p.3072-3076
Main Authors: Wang, Rui, Wang, Lili, Xu, Qin, Ren, Bao-Yi, Liang, Fushun
Format: Article
Language:English
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Summary:A visible-light-promoted electron-donor–acceptor (EDA) complex-initiated [5 + 1] annulation between biguanides and perfluoroalkyl halides for the construction of perfluoroalkyl-s-triazines has been developed. It was found that both visible light and dioxygen in the air are favorable for the reaction. A radical–polar crossover mechanism was proposed, in which sequential SET, radical combination, HF elimination, electrocyclization, and aromatization are involved.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00655