Cofactor-free biocatalytic hydrogenation of nitro compounds for synthesis of amines

• DOI: 10.26434/chemrxiv-2024-vqfc1
• Publication Date: 2024-01-29T08:44:37Z
• Authors: Daria Sokolova; Tara Lurshay; Jack Rowbotham; Georgia Stonadge; Holly Reeve; Sarah Cleary; Tim Sudmeier; Kylie Vincent
• Keywords: Biocatalysis

We report a new paradigm for chemoselective hydrogenation of nitro compounds to amines, under mild, aqueous conditions. Hydrogenase enzyme releases electrons from H2 carbon black support which facilitates nitro-group reduction. For 30 nitroarenes we demonstrate full conversion (isolated yields 78 – 96%), with products including pharmaceuticals benzocaine, procainamide and mesalazine, 4-aminophenol precursor acetaminophen (paracetamol). also showcase gram-scale synthesis 90% isolated yield. potential extension aliphatic substrates. The catalyst is highly selective reduction the group over other unsaturated bonds, tolerant wide range functional groups, exhibits excellent stability in reactions lasting up 72 hours reusability 5 cycles, indicating scope direct translation fine chemical manufacturing.