Issue 32, 2022

Catalytic aerobic photooxidation of triarylphosphines using dibenzo-fused 1,4-azaborines

Abstract

Although dibenzo-fused 1,4-heteroaromatics are utilized as strongly reducing photocatalysts in organic synthesis and polymerization, they have rarely been employed in catalytic photooxidation. Moreover, to date, their boron-analogs, dibenzo-fused 1,4-azaborines (DBABs), have not been applied in photocatalysis despite their promising potential as photocatalysts. Accordingly, herein, aerobic photooxidation of triarylphosphines (Ar3P) was performed using DBABs as photocatalysts. The reaction smoothly proceeded in an aprotic solvent, and phosphine oxides were obtained in appropriate yields. Density functional theory calculations suggested that DBAB captured and activated phosphadioxirane intermediates, which were generated by the interaction of Ar3P with 1O2, at the Lewis acidic boron center.

Graphical abstract: Catalytic aerobic photooxidation of triarylphosphines using dibenzo-fused 1,4-azaborines

Supplementary files

Article information

Article type
Communication
Submitted
08 Feb 2022
Accepted
23 Mar 2022
First published
23 Mar 2022

Chem. Commun., 2022,58, 5001-5004

Catalytic aerobic photooxidation of triarylphosphines using dibenzo-fused 1,4-azaborines

M. Kondo and T. Agou, Chem. Commun., 2022, 58, 5001 DOI: 10.1039/D2CC00782G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements