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

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

研究成果: Article同行評審

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.

原文English
頁(從 - 到)6180-6184
頁數5
期刊Organic Chemistry Frontiers
10
發行號24
DOIs
出版狀態Published - 2023 10月 24

All Science Journal Classification (ASJC) codes

  • 有機化學

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