Selective N-monomethylation of primary anilines with the controllable installation of N-CH2D, N-CHD2, and N-CD3 units

Jing Meng; Hui-Min Xia; Ai-Qing Xu; Yi-Feng Wang; Zhijuan Wang; Feng-Lian Zhang

doi:10.1039/D0OB01054E

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Selective N-monomethylation of primary anilines with the controllable installation of N-CH₂D, N-CHD₂, and N-CD₃ units†

Jing Meng,^a Hui-Min Xia,^b Ai-Qing Xu,^b Yi-Feng Wang,

^b Zhijuan Wang

*^a and Feng-Lian Zhang

*^b

Author affiliations

* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China
E-mail: ias_zjwang@njtech.edu.cn

^b Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China
E-mail: zfl9@ustc.edu.cn

Abstract

The selective N-monomethylation of primary anilines was realized by the use of the Me₃N-BH₃/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH₂D, N-CHD₂, and N-CD₃ units with high levels of deuterium incorporation using Me₃N-BH₃/d₇-DMF, Me₃N-BD₃/DMF and Me₃N-BD₃/d₇-DMF systems, respectively.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01054E
Article type: Communication
Submitted: 21 May 2020
Accepted: 12 Jun 2020
First published: 12 Jun 2020

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Org. Biomol. Chem., 2020,18, 4922-4926

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Selective N-monomethylation of primary anilines with the controllable installation of N-CH₂D, N-CHD₂, and N-CD₃ units

J. Meng, H. Xia, A. Xu, Y. Wang, Z. Wang and F. Zhang, Org. Biomol. Chem., 2020, 18, 4922 DOI: 10.1039/D0OB01054E

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Organic & Biomolecular Chemistry