ReviewChemistry (Weinheim an der Bergstrasse, Germany)2022
Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities.
Review in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Enantioselective Copper-Catalyzed Synthesis of Hydroxylamines via Hydrofunctionalization of Alkenes using Nitroalkanes.Journal of the American Chemical Society · 2026Article
- Fully Biobased Epoxy-Imine Monomer: Synthesis and Curing with Amines Toward Vitrimeric Materials.ACS sustainable chemistry & engineering · 2026Article
- Article
- Enantioselective NHC-Catalyzed Annulation via Umpolung for the Construction of Hydroxylamine Architectures with Variable Ring Sizes.Organic letters · 2025Article
- Ceria-Zirconia-Supported Pt as an Efficient Catalyst for the Sustainable Synthesis of Hydroxylamines and Primary Amines via the Hydrogenation of Oximes Under Ambient Conditions.Molecules (Basel, Switzerland) · 2025Article
- An Unexpected Formation of Spiro Isoxazoline-Dihydrofurane Compounds from Substituted Ketofurfuryl Alcohols.Molecules (Basel, Switzerland) · 2024Article
- Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines.Molecules (Basel, Switzerland) · 2023Review
- Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
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2 authors.
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Abstract
Catalytic reduction of oximes represents a direct efficient approach to synthesize valuable hydroxylamine derivatives. However this transformation presents significant challenges: oximes are hard to reduce and, if reactive, reductive cleavage of the weak N-O bond often leads to primary amine side products. The first suitable systems involved the use of platinum-based heterogeneous catalysts with hydrogen as reductant and stoichiometric amounts of a strong Brønsted acid. More recently metal-free and transition-metal-based homogeneous catalysts have been developed, which display the highest turnovers (up to 4000). In the asymmetric variants, the E/Z-geometry of the oxime double bond affects significantly the stereoselectivity, sometimes requiring extra synthetic efforts in substrate preparation. This minireview provides an overview of the advances and limitations in catalytic oxime to hydroxylamine reduction. Emphasis is put on highlighting and comparing the practical aspects of the existing methods, such as their reaction conditions and substrate scope. Additionally, future directions for improving this young research area are suggested.
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