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 Eph 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

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