Green and Efficient Benzylation of Amines Using Copper Catalysts under Microwave Irradiation
Abstract
N-Benzylation of aliphatic, aromatic, and heteroaromatic amines was performed in the presence of metallic copper and environmentally benign bases by conventional and microwave heating. The ethanol-water mixture was found to be a suitable solvent, enabling improved product formation, especially under microwave irradiation. We obtained with this protocol a good conversion (up to 86%) in only 6 h, the time was reduced to 30 min under microwave irradiation. The steric and electronic effects were also explored to provide further insight into the suitability of these protocols. The catalyst was recovered and reused to afford the product without significant loss of mass and catalytic properties.
Keywords
Thanks
References
- 1. Natte K, Jagadeesh R V. Amines by reduction. In: Kirk-Othmer Encyclopedia of Chemical Technology. Wiley; 2021. p. 1–34. Available from:
. - 2. Zhou L, Li F, Xu HB, Luo CX, Wu HY, Zhu MM, et al. Treatment of cerebral ischemia by disrupting ischemia-induced interaction of nNOS with PSD-95. Nat Med. 2010 Dec 21;16(12):1439–43. Available from:
. - 3. Arslan M, Duymuş H, Yakuphanoglu F. Optical properties of the poly(N-benzylaniline) thin film. J Phys Chem B. 2006 Jan 1;110(1):276–80. Available from:
. - 4. Li B, Yu J, Li C, Li Y, Luo J, Shao Y. “One pot” synthesis of tertiary amines: Ru(II) catalyzed direct reductive N -benzylation of imines with benzyl bromide derivatives. Tetrahedron Lett. 2017 Jan;58(2):137–41. Available from:
. - 5. Huang L, Wang Z, Geng L, Chen R, Xing W, Wang Y, et al. Selective and recyclable rhodium nanocatalysts for the reductive N-alkylation of nitrobenzenes and amines with aldehydes. RSC Adv. 2015;5(70):56936–41. Available from:
. - 6. Nuzhdin AL, Artiukha EA, Bukhtiyarova GA, Derevyannikova EA, Bukhtiyarov VI. Synthesis of secondary amines by reductive amination of aldehydes with nitroarenes over supported copper catalysts in a flow reactor. Catal Commun. 2017 Dec;102:108–13. Available from:
. - 7. Wei D, Bruneau-Voisine A, Valyaev DA, Lugan N, Sortais JB. Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant. Chem Commun. 2018;54(34):4302–5. Available from:
. - 8. Ikawa T, Fujita Y, Mizusaki T, Betsuin S, Takamatsu H, Maegawa T, et al. Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines. Org Biomol Chem. 2012;10(2):293–304. Available from:
.
Details
Primary Language
English
Subjects
Organic Chemical Synthesis
Journal Section
Research Article
Publication Date
June 3, 2026
Submission Date
March 9, 2026
Acceptance Date
May 6, 2026
Published in Issue
Year 2026 Volume: 2026 Number: 2
