Selective hydrogenation of nitro compounds to amines by coupled redox reactions over a heterogeneous biocatalyst.

ABSTRACT: Cleaner synthesis of amines remains a key challenge in organic chemistry because of their prevalence in pharmaceuticals, agrochemicals and synthetic building blocks. Here, we report a different paradigm for chemoselective hydrogenation of nitro compounds to amines, under mild, aqueous conditions. The hydrogenase enzyme releases electrons from H₂ to a 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, and 4-aminophenol - precursor to paracetamol (acetaminophen). We also showcase gram-scale synthesis of procainamide with 90% isolated yield. We demonstrate potential for extension to aliphatic substrates. The cataly

SUBMITTER: Sokolova D 

PROVIDER: S-EPMC11344822 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature