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Selective N ‐Monomethylation of Anilines with Methanol Catalyzed by Commercial Pd/C as an Efficient and Reusable Catalyst
Author(s) -
Jiang Lei,
Guo Fang,
Wang Yinran,
Jiang Jialin,
Duan Yangzhi,
Hou Zhaomin
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900509
Subject(s) - chemistry , catalysis , aniline , methanol , reagent , yield (engineering) , organic chemistry , selectivity , combinatorial chemistry , formaldehyde , materials science , metallurgy
N ‐methylation of amines is one of the most important C−N bond‐forming reactions and is widely utilized for the synthesis of numerous agrochemicals, drugs, natural products, and dyes. In this paper, the N ‐monomethylation of aniline derivatives using Pd/C catalyst and methanol as the methylation reagent was investigated. The N ‐monomethylation of various anilines was achieved with high activity and selectivity under relatively mild reaction conditions, and the yield of N ‐monomethyl anilines was over 90 %. Notably, the commercial, readily available, and inexpensive heterogeneous catalyst, Pd/C, could be easily recovered and reused more than five times with only a slight decrease in activity; gram‐scale experiments were also successfully performed.