Aerobic oxidation/metal-free cyclization cascades of nitrosoarenes and allenynes with TEMPO/O2: a switch of diradical to single radical intermediates

文献情報

出版日 2023-10-24

DOI 10.1039/D3QO01466E

インパクトファクター 5.281

著者

Chandrima Maitra, Debashis Barik, Yeu-Shiuan Ho, Mu-Jeng Cheng, Rai-Shung Liu

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

Aerobic oxidation/metal-free cyclization cascades of nitrosoarenes and allenynes with TEMPO/O2: a switch of diradical to single radical intermediates

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