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

Author:
Wang, Rui, Wang, Lili, Xu, Qin, Ren, Bao-Yi, Liang, Fushun
Source:
Organic letters 2019 v.21 no.9 pp. 3072-3076
ISSN:
1523-7052
Subject:
air, aromatization, biguanides, chemical structure, light, oxygen, perfluorocarbons
Abstract:
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.
Agid:
6397596