Issue 5, 2021

Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

Abstract

Reported here is an intermolecular pyridylation/phosphinoylation of alkenes using 4-cyanopyridine and diphenylphosphine oxide under visible-light-induced organic photoredox catalysis. The reaction occurs under mild metal-free conditions, possessing a broad substrate scope. The protocol can be practiced on a gram scale and applied to the modification of natural product-derived and medicinally relevant complex molecules containing a styrene unit. Mechanistic investigations suggest that triethylamine serves as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents.

Graphical abstract: Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

Supplementary files

Article information

Article type
Research Article
Submitted
06 Oct 2020
Accepted
21 Dec 2020
First published
22 Dec 2020

Org. Chem. Front., 2021,8, 901-907

Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

J. Shen, Y. Zhang, Y. Yu and M. Wang, Org. Chem. Front., 2021, 8, 901 DOI: 10.1039/D0QO01218A

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