Efficient Cobalt-Catalyzed Methylation of Amines Using Methanol

Zhenghui Liu; Zhenzhen Yang; Xiaoxiao Yu; Hongye Zhang; Bo Yu; Yanfei Zhao; Zhimin Liu

doi:10.1002/adsc.201701044

Efficient Cobalt-Catalyzed Methylation of Amines Using Methanol

Zhenghui Liu, Zhenzhen Yang, Xiaoxiao Yu, Hongye Zhang, Bo Yu, Yanfei Zhao, Zhimin Liu

Research output: Contribution to journal › Article › peer-review

98 Scopus citations

Abstract

The methylation of amines using methanol is a promising route to synthesize N-methylamines, and the development of cheap and efficient catalytic system for this reaction is of great significance. Herein, we reported a cobalt (Co)-based catalytic system, which was in situ formed from commercially available Co precursor and a tetradentate phosphine ligand P(CH₂CH₂PPh₂)₃ combined with K₃PO₄. This catalystic system was very effective for the selective production of dimethylated products from aliphatic amines and monomethylated ones from aromatic amines. The reaction mechanism was further investigated by control and isotope labelling experiments. (Figure presented.).

Original language	English
Pages (from-to)	4278-4283
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	24
DOIs	https://doi.org/10.1002/adsc.201701044
State	Published - Dec 19 2017
Externally published	Yes

Funding

The authors thank the National Natural Science Foundation of China (Nos. 21673256, 21402208, 21403252).

Funders	Funder number
National Natural Science Foundation of China	21402208, 21673256, 21403252

Keywords

Alkylation
Amines
Cobalt
C−N bond formation
homogeneous catalysis

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10.1002/adsc.201701044

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abstract = "The methylation of amines using methanol is a promising route to synthesize N-methylamines, and the development of cheap and efficient catalytic system for this reaction is of great significance. Herein, we reported a cobalt (Co)-based catalytic system, which was in situ formed from commercially available Co precursor and a tetradentate phosphine ligand P(CH2CH2PPh2)3 combined with K3PO4. This catalystic system was very effective for the selective production of dimethylated products from aliphatic amines and monomethylated ones from aromatic amines. The reaction mechanism was further investigated by control and isotope labelling experiments. (Figure presented.).",

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AU - Liu, Zhenghui

AU - Yang, Zhenzhen

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AU - Zhang, Hongye

AU - Yu, Bo

AU - Zhao, Yanfei

AU - Liu, Zhimin

PY - 2017/12/19

Y1 - 2017/12/19

N2 - The methylation of amines using methanol is a promising route to synthesize N-methylamines, and the development of cheap and efficient catalytic system for this reaction is of great significance. Herein, we reported a cobalt (Co)-based catalytic system, which was in situ formed from commercially available Co precursor and a tetradentate phosphine ligand P(CH2CH2PPh2)3 combined with K3PO4. This catalystic system was very effective for the selective production of dimethylated products from aliphatic amines and monomethylated ones from aromatic amines. The reaction mechanism was further investigated by control and isotope labelling experiments. (Figure presented.).

AB - The methylation of amines using methanol is a promising route to synthesize N-methylamines, and the development of cheap and efficient catalytic system for this reaction is of great significance. Herein, we reported a cobalt (Co)-based catalytic system, which was in situ formed from commercially available Co precursor and a tetradentate phosphine ligand P(CH2CH2PPh2)3 combined with K3PO4. This catalystic system was very effective for the selective production of dimethylated products from aliphatic amines and monomethylated ones from aromatic amines. The reaction mechanism was further investigated by control and isotope labelling experiments. (Figure presented.).

KW - Alkylation

KW - Amines

KW - Cobalt

KW - C−N bond formation

KW - homogeneous catalysis

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Efficient Cobalt-Catalyzed Methylation of Amines Using Methanol

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