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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
Parent Title (English):Chemistry - A European Journal
First Page:e202201307
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
Research Groups:Innovative Electron Microscopy
DDC classes:500 Naturwissenschaften und Mathematik / 540 Chemie
Open Access:Open Access
Signature:INM 2022/057
Licence (German):License LogoCreative Commons - CC BY - Namensnennung 4.0 International