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Visible‐Light Catalyzed [1+2+2] Cycloaddition Reactions Enabled by the Formation of Methylene Nitrones.

Authors :
Guo, Jing
Xie, Ying
Zeng, Wen‐Tian
Wu, Qiao‐Lei
Weng, Jiang
Lu, Gui
Source :
Advanced Synthesis & Catalysis. 12/8/2020, Vol. 362 Issue 23, p5450-5456. 7p.
Publication Year :
2020

Abstract

Nitrones are key intermediates in organic synthesis. Herein, we report the first photo‐redox synthesis of methylene nitrone intermediates from nitroarenes and arylamines. The highly reactive methylene nitrones are in situ trapped by alkenes to afford various isoxazolidines. This three‐component reaction features the use of N,N‐dimethylanilines or N‐aryl glycines as C1 building blocks, which allow for the one‐pot formal [1+2+2] cycloaddition from simple starting materials. A wide range of useful isoxazolidines can be obtained under mild conditions with moderate to good yields. Mechanistic investigations support the formation of methylene nitrone via selective N−CH3 bond cleavage and methylene transfer. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
16154150
Volume :
362
Issue :
23
Database :
Academic Search Index
Journal :
Advanced Synthesis & Catalysis
Publication Type :
Academic Journal
Accession number :
147478229
Full Text :
https://doi.org/10.1002/adsc.202000858