Photoinduced synthesis of functionalized oxetanes via diradical-mediated ring contraction. Issue 13 (13th June 2022)

• Record Type: Journal Article
• Authors: Qi, Dan; Bai, Jinrui; Zhang, Haoxiang; Li, Bin; Song, Zhuoheng; Ma, Na; Guo, Lin; Song, Lijuan; Xia, Wujiong
• Is Part Of: Green chemistry. Volume 24:Issue 13(2022)
• Page Start: 5046
• Page End: 5051
• Publication Date: 2022-06-13
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc01362b
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A photochemical ring contraction is reported for the synthesis of oxetanes from dihydrofurans and diazo compounds under catalyst-free conditions. 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.