Selective Catalytic Hydrogenation of Nitro Groups in the Presence of Activated Heteroaryl Halides

• Published in: Journal of organic chemistry Vol. 76; no. 23; pp. 9841 - 9844
• Main Authors: Kasparian, Annie J, Savarin, Cecile, Allgeier, Alan M, Walker, Shawn D
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.12.2011; Amer Chemical Soc
• Subjects: Amines - chemical synthesis; Amines - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Hydrocarbons, Halogenated - chemistry; Hydrogenation; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; TEMPERATURE; REDUCTION; NITROARENES; Nitro compound; Catalytic reaction; Isoquinoline derivatives; Dehalogenation; Chemoselectivity; Nitrogen heterocycle; Transition metal; Selectivity; Hydrogenation; Organic halogen compounds; Chemical reduction; Amine; Platinum; By product; Catalyst; Heterocyclic compound; Low temperature
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo2015664

Chemoselective reduction of nitro groups in the presence of activated heteroaryl halides was achieved via catalytic hydrogenation with a commercially available sulfided platinum catalyst. The optimized conditions employ low temperature, pressure, and catalyst loading (<0.1 mol % Pt) to afford heteroaromatic amines with minimal hydrodehalogenation byproducts.