![N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure](https://cnstatic.chemtradehub.com/structs/210/2101206-92-0-2eb5.webp "N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure")
Aerobic oxidation/metal-free cyclization cascades of nitrosoarenes and allenynes with TEMPO/O2: a switch of diradical to single radical intermediates
文献信息
发布日期
2023-10-24
DOI
10.1039/D3QO01466E
影响因子
5.281
作者
Chandrima Maitra, Debashis Barik, Yeu-Shiuan Ho, Mu-Jeng Cheng, Rai-Shung Liu
查看原文
摘要
New cascade oxidative cyclizations between nitrosoarenes and allenynes in the presence of TEMPO/O2 mixtures afford new indanones fused with an aziridine ring. These four-component reactions are catalyst- and additive-free, yielding no byproducts with nearly 100% atom economy. Our DFT calculations indicate that the nitrosoarene/allenyne mixtures generate diradical intermediates that are intercepted by a TEMPO radical to form a single nitroxy radical to take up one O2 molecule. This reaction model can also rationalize new chemoselectivity for nitrosoarenes bearing para-alkyl substituents.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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