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

Daria Sokolova, Tara C. Lurshay, Jack S. Rowbotham, Georgia Stonadge, Holly A. Reeve, Sarah E. Cleary (), Tim Sudmeier () and Kylie A. Vincent ()
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Daria Sokolova: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Tara C. Lurshay: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Jack S. Rowbotham: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Georgia Stonadge: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Holly A. Reeve: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Sarah E. Cleary: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Tim Sudmeier: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road
Kylie A. Vincent: University of Oxford, Inorganic Chemistry Laboratory, South Parks Road

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: 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 catalyst is highly selective for reduction of the nitro group over other unsaturated bonds, tolerant to a wide range of functional groups, and exhibits excellent stability in reactions lasting up to 72 hours and full reusability over 5 cycles with a total turnover number over 1 million, indicating scope for direct translation to fine chemical manufacturing.

Date: 2024
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DOI: 10.1038/s41467-024-51531-2

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