Issue 13, 2022

Photoinduced synthesis of functionalized oxetanes via diradical-mediated ring contraction

Abstract

A versatile photochemical ring contraction is reported for the synthesis of oxetanes under catalyst-free conditions. The reaction is enabled by the use of 2,5-dihydrofurans and diazo compounds under visible light irradiation, delivering functionalized 3-vinyloxetanes as major products. The outstanding features of this protocol include mild reaction conditions, operational simplicity and scalability, as well as excellent functional-group tolerance. DFT calculations indicate that the reaction may proceed through the formation of an oxonium ylide intermediate followed by a diradical-mediated rearrangement and cyclization.

Graphical abstract: Photoinduced synthesis of functionalized oxetanes via diradical-mediated ring contraction

Supplementary files

Article information

Article type
Communication
Submitted
09 abr 2022
Accepted
06 jun 2022
First published
08 jun 2022

Green Chem., 2022,24, 5046-5051

Photoinduced synthesis of functionalized oxetanes via diradical-mediated ring contraction

D. Qi, J. Bai, H. Zhang, B. Li, Z. Song, N. Ma, L. Guo, L. Song and W. Xia, Green Chem., 2022, 24, 5046 DOI: 10.1039/D2GC01362B

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