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Visible‐Light Catalyzed [1+2+2] Cycloaddition Reactions Enabled by the Formation of Methylene Nitrones
Author(s) -
Guo Jing,
Xie Ying,
Zeng WenTian,
Wu QiaoLei,
Weng Jiang,
Lu Gui
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000858
Subject(s) - nitrone , chemistry , methylene , cycloaddition , photochemistry , catalysis , bond cleavage , combinatorial chemistry , organic chemistry
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−CH 3 bond cleavage and methylene transfer.