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

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6180-6184
Number of pages5
JournalOrganic Chemistry Frontiers
Volume10
Issue number24
DOIs
Publication statusPublished - 2023 Oct 24

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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