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N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate

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Abstract

Dimethyl carbonate (DMC), an environmentally friendly methylation agent, is a substitute for traditional methylation agents such as methyl halides (CH3X, X = I, Br, Cl) or dimethyl sulfate. An efficient, convenient, and green method has been developed for N-methylation of poorly nucleophilic aromatic amines with DMC. It was found that the couple PEG400/K2CO3 provides good selectivity for the N-methylation product. Finally, the mechanism for reaction of amines with DMC was investigated, and a plausible multistep mechanism proposed and verified.

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Acknowledgments

The authors acknowledge the Key Planning Project of Science and Technology of Fujian Province, China (Grant Number 2014N0020) for financial support.

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Authors and Affiliations

  1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, People’s Republic of China

    Huidong Yan, Liufang Zeng, Yaqiang Xie, Yu Cui, Liyi Ye & Song Tu

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  1. Huidong Yan
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  2. Liufang Zeng
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  3. Yaqiang Xie
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  4. Yu Cui
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  5. Liyi Ye
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Correspondence to Song Tu.

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Yan, H., Zeng, L., Xie, Y. et al. N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate. Res Chem Intermed 42, 5951–5960 (2016). https://doi.org/10.1007/s11164-015-2416-4

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