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Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies

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Abstract

This work describes an efficient α-phosphorylation of a wide variety of N-aryl tertiary amines under mild conditions. It consists of a simple combination of amines (electron donors) with N-ethoxy-2-methylpyridinium tetrafluoroborate (electron acceptor) in the presence of P(V)–H compounds under visible light irradiation. Physical organic investigations support the formation of an electron-donor–acceptor complex (amine/pyridinium ion) as a key intermediate.

Graphical abstract: Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies

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Publication details

The article was received on 10 Sep 2018, accepted on 09 Nov 2018 and first published on 12 Nov 2018


Article type: Research Article
DOI: 10.1039/C8QO00985F
Citation: Org. Chem. Front., 2019, Advance Article
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    Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies

    V. Quint, N. Chouchène, M. Askri, J. Lalevée, A. Gaumont and S. Lakhdar, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO00985F

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