Electrochemical Amination of Aryl Halides with NH3
- PMID: 40202031
- DOI: 10.1002/anie.202504459
Electrochemical Amination of Aryl Halides with NH3
Abstract
Primary arylamines are the most pivotal class of organic motifs in pharmaceuticals, agrochemicals, ligands and natural products. Ammonia (NH3) is an ideal nitrogen source in terms of reactivity, atom economy, and environmental compatibility. Despite significant progress in the synthesis of primary arylamines, the development of a general method for rapid access to diversely functionalized primary arylamines is still urgent and necessary. Herein, we developed a method for the direct synthesis of primary arylamines through electrochemical amination of aryl halides with NH3. Notably, the weak nucleophilic reagent NH3 was directly used as an ammonia surrogate, allowing for efficient conversion of carbon-halogen bonds to diverse primary arylamines with good functional group tolerance. A broad scope of functionalized primary arylamines has been achieved in moderate to excellent yields.
Keywords: Amination; Aryl halides; Electrochemistry; NH3; Primary arylamines.
© 2025 Wiley‐VCH GmbH.
Similar articles
-
Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.Acc Chem Res. 2008 Nov 18;41(11):1534-44. doi: 10.1021/ar800098p. Acc Chem Res. 2008. PMID: 18681463 Free PMC article.
-
Electrogenerated Nickel Catalyst for C-N Cross-Coupling.J Org Chem. 2023 Jan 6;88(1):675-683. doi: 10.1021/acs.joc.2c01964. Epub 2022 Dec 14. J Org Chem. 2023. PMID: 36516437
-
New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C-H Amination.Chemistry. 2017 Sep 7;23(50):12096-12099. doi: 10.1002/chem.201701979. Epub 2017 Jul 10. Chemistry. 2017. PMID: 28605084
-
Direct amination of aryl halides with ammonia.Chem Soc Rev. 2010 Nov;39(11):4130-45. doi: 10.1039/c003692g. Epub 2010 Sep 28. Chem Soc Rev. 2010. PMID: 20877862 Review.
-
[Synthetic studies on natural products with aromatic nitrogen heterocycles based on development of the methods for the formation of aryl carbon-nitrogen bond].Yakugaku Zasshi. 2013;133(10):1065-78. doi: 10.1248/yakushi.13-00189. Yakugaku Zasshi. 2013. PMID: 24088350 Review. Japanese.
Cited by
-
Electrochemically promoted defluorinative sulfoximination and fluorosulfonylation of non-activated aryl fluorides at room temperature.Chem Sci. 2025 Jul 1;16(31):14161-14169. doi: 10.1039/d5sc03674g. eCollection 2025 Aug 6. Chem Sci. 2025. PMID: 40630635 Free PMC article.
References
-
- H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 2015, 115, 3388–3432.
-
- P. Ruiz‐Castillo, S. L. Buchwald, Chem. Rev. 2016, 116, 12564–12649.
-
- J. A. Smith, B. C. Johnson, J. Med. Chem. 2020, 63, 6543–6572.
-
- L. Wang, X. Zhang, Cancer Res. Rev. 2019, 45, 234–250.
-
- R. T. Brown, M. L. Davis, Eur. J. Med. Chem. 2018, 150, 1–15.
Grants and funding
LinkOut - more resources
Full Text Sources