Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
30 ذو الحجة 1439
Accepted
01 ربيع الأول 1440
First published
04 ربيع الأول 1440

Org. Chem. Front., 2019,6, 41-44

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, 6, 41 DOI: 10.1039/C8QO00985F

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