Selective N,N-dimethylation of primary aromatic amines with dimethyl carbonate in the presence of diphenylammonium triflate

Shen, Zhen; Jiang, Xiaolei

doi:10.1016/j.molcata.2003.12.008

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Cited by 16 publications

(1 citation statement)

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“…This can decrease the activation energy and promote methylation reactions. 18,19 Highly polar solvents such as H 2 O, N , N -dimethylformamide (DMF), and methanol therefore improve the selectivity for methylation.…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free N-methylation of 3-methylxanthine with dimethyl carbonate in water: green synthesis of theobromine

Yang

Wang

et al. 2022

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Catalyst-free N-methylation of 3-methylxanthine with dimethyl carbonate in water: green synthesis of theobromine

Yang

Wang

et al. 2022

New J. Chem.

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N ‐methylation

Crosby¹

2020

Catalysis From a to Z

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Highly Efficient N‐Monomethylation of Primary Aryl Amines

Peng¹,

Liu

Tang

et al. 2009

Chin. J. Chem.

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A highly efficient method for specific synthesis of N-monomethylarylamines is presented. Anilines were treated with acetic anhydride and triethylamine in dry CH 2 Cl 2 to give the corresponding acetamides. The subsequent N-monomethylation of acetyl aryl amines with methyl iodide and NaH in THF introduced methyl group. Acid hydrolysis of the N-methyl acetanilides in ethylene glycol generated the corresponding N-methyl-N-aryl amines in high yields. This method was also used to synthesize (E)-2-bromo-5-(4-methylaminostyryl)pyridine that may be useful as an amyloid imaging agent for Alzheimer's disease.

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Selective N,N-dimethylation of primary aromatic amines with dimethyl carbonate in the presence of diphenylammonium triflate

Cited by 16 publications

References 28 publications

Catalyst-free N-methylation of 3-methylxanthine with dimethyl carbonate in water: green synthesis of theobromine

Catalyst-free N-methylation of 3-methylxanthine with dimethyl carbonate in water: green synthesis of theobromine

N ‐methylation

Highly Efficient N‐Monomethylation of Primary Aryl Amines

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