Journal article
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 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.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.6MB, Terms of use)
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(Preview, Supplementary materials, pdf, 4.3MB, Terms of use)
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- Publisher copy:
- 10.1038/s41467-024-51531-2
Authors
+ European Research Council
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- Funder identifier:
- https://ror.org/0472cxd90
- Grant:
- 819580
+ Engineering and Physical Sciences Research Council
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- Funder identifier:
- https://ror.org/0439y7842
- Grant:
- EP/N013514/1
- 515587
+ Biotechnology and Biological Sciences Research Council
More from this funder
- Funder identifier:
- https://ror.org/00cwqg982
- Grant:
- BB/X002624/1
- Publisher:
- Springer Nature
- Journal:
- Nature Communications More from this journal
- Volume:
- 15
- Issue:
- 1
- Article number:
- 7297
- Place of publication:
- England
- Publication date:
- 2024-08-24
- Acceptance date:
- 2024-08-11
- DOI:
- EISSN:
-
2041-1723
- Pmid:
-
39181899
- Language:
-
English
- Pubs id:
-
2024377
- Local pid:
-
pubs:2024377
- Deposit date:
-
2024-09-21
Terms of use
- Copyright holder:
- Sokolova et al
- Copyright date:
- 2024
- Rights statement:
- ©2024 The Authors. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder.
- Licence:
- CC Attribution (CC BY)
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