Issue 22, 2022

Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions

Abstract

Over the past two decades, visible-light-induced transformations have been regarded as being among the most environmentally benign and powerful strategies for constructing complex molecules and diverse synthetic building blocks in organic synthesis. However, the development of efficient photochemical processes for assembling enantiomerically pure molecules remains a significant challenge. Herein, we describe a simple and efficient visible-light-induced C–P bond forming reaction for the synthesis of P-chiral heteroaryl phosphine oxides in moderate to high yields with excellent ee values (97–99% ee). Even in the absence of transition metal or photoredox catalysts, a variety of P-chiral heteroaryl phosphine oxides, including chiral diphosphine oxide 41, have been directly obtained under air conditions. Density functional theory (DFT) calculations have shown that the reaction involves intersystem crossing and single electron transfer to give a diradical intermediate under visible light irradiation.

Graphical abstract: Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions

Supplementary files

Article information

Article type
Edge Article
Submitted
05 yan 2022
Accepted
11 apr 2022
First published
25 apr 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 6519-6524

Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions

Y. Zhang, J. Yuan, G. Huang, H. Yu, J. Liu, J. Chen, S. Meng, J. Zhong, L. Dang, G. Yu and C. Che, Chem. Sci., 2022, 13, 6519 DOI: 10.1039/D2SC00036A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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