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 language | English |
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Pages (from-to) | 6180-6184 |
Number of pages | 5 |
Journal | Organic Chemistry Frontiers |
Volume | 10 |
Issue number | 24 |
DOIs | |
Publication status | Published - 2023 Oct 24 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry