Photoinduced transition-metal and external photosensitizer free phosphonation of unactivated C(sp2)–F bond via SET process under mild conditions

Autor: Qian Dou, Yatao Lang, Huiying Zeng, Chao-Jun Li
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Fundamental Research, Vol 1, Iss 6, Pp 742-746 (2021)
Druh dokumentu: article
ISSN: 2667-3258
DOI: 10.1016/j.fmre.2021.06.018
Popis: Transition-metal catalyzed cross-couplings of aryl halides (ArI, ArBr and ArCl) with a broad range of nucleophiles have been developed as powerful methods for carbon–carbon and carbon–heteroatom bonds formation. However, due to the high bond dissociation energy of unactivated C(sp2)–F, cross-couplings of mono-fluoroarenes are the most challenging, especially without using transition-metal catalysts. Herein, a photo-induced transition-metal and external photosensitizer free defluorophosphonation of monofluoroarenes via unactivated C(sp2)–F bond cleavage is reported. Different mono-fluoroarenes have been successfully cross-coupled with dialkyl phosphites in moderate to excellent yields under mild conditions. Mechanistic studies have revealed the possible involvement of a photo-induced SET process and aryl free radical intermediates.
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