Abstract
As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.
| Original language | English |
|---|---|
| Pages (from-to) | 6199-6203 |
| Number of pages | 5 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2018 |
| Issue number | 45 |
| DOIs | |
| Publication status | Published - 6 Dec 2018 |
Keywords
- Acylnitroso
- Catalysis
- Cycloaddition
- Ene reaction
- Iodine
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Uraoka, S., Shinohara, I., Shimizu, H., Noguchi, K., Yoshimura, A., Zhdankin, V. V., & Saito, A. (2018). Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis. European Journal of Organic Chemistry, 2018(45), 6199-6203. https://doi.org/10.1002/ejoc.201801340