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Selective hydrogenation of nitro compounds to amines by coupled redox reactions over a heterogeneous biocatalyst
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Selective hydrogenation of nitro compounds to amines by coupled redox reactions over a heterogeneous biocatalyst
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Journal Article
Selective hydrogenation of nitro compounds to amines by coupled redox reactions over a heterogeneous biocatalyst
2024
Overview
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 H
2
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.
The reduction of nitro-groups is a common synthetic route to amines, but biocatalytic strategies for such reactions are still being developed. In this study, the authors repurposed the hydrogenase enzyme by immobilisation on carbon black to yield a heterogeneous chemobiocatalyst for selective production of amines.
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