Synthesis of 3,4-Dihydro-2H-pyrroles from Ketones, Aldehydes, and Nitro Alkanes via Hydrogenative Cyclization
- Syntheses of N-heterocyclic compounds that permit a flexible introduction of various substitution patterns using inexpensive and diversely available starting materials are highly desirable. Easy to handle and reusable catalysts based on earth-abundant metals are especially attractive for these syntheses. We report here on the synthesis of 3,4-dihydro-2H-pyrroles via the hydrogenation and cyclization of nitro ketones. The latter are easily accessible from three components: a ketone, an aldehyde and a nitroalkane. Our reaction has a broad scope and 23 of the 33 products synthesized are compounds which have not yet been reported. The key to the general hydrogenation/cyclization reaction is a highly active, selective and reusable nickel catalyst, which was identified from a library of 24 earth-abundant metal catalysts.
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| Document Type: | Article |
|---|---|
| Author: | Barbara Klausfelder, Patricia S. Blach, Niels de JongeORCiD, Rhett KempeORCiD |
| URN: | urn:nbn:de:bsz:291:415-1870 |
| DOI: | https://doi.org/10.1002/chem.202201307 |
| Parent Title (English): | Chemistry - A European Journal |
| Volume: | 28 |
| Issue: | 47 |
| First Page: | e202201307 |
| Language: | English |
| Year of first Publication: | 2022 |
| Release Date: | 2022/09/28 |
| Tag: | catalysis; hydrogenation; multi component reaction; n-heterocycles; nickel |
| Impact: | 05.020 (2021) |
| Funding Information: | Deutsche Forschungsgemeinschaft KE 756/ 34–1 |
| Scientific Units: | Innovative Electron Microscopy |
| DDC classes: | 500 Naturwissenschaften und Mathematik / 540 Chemie |
| Open Access: | Open Access |
| Signature: | INM 2022/057 |
| Licence (German): |  Creative Commons - CC BY - Namensnennung 4.0 International |
