Communication

Selective N-Alkylation of Amines with Alcohols by Using Non-Metal-Based Acid–Base Cooperative Catalysis

  1. Dr. Ya Du1,3,
  2. Shunsuke Oishi1,
  3. Dr. Susumu Saito1,2,*

Article first published online: 21 SEP 2011

DOI: 10.1002/chem.201102446

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 17, Issue 44, pages 12262–12267, October 24, 2011

Additional Information

How to Cite

Du, Y., Oishi, S. and Saito, S. (2011), Selective N-Alkylation of Amines with Alcohols by Using Non-Metal-Based Acid–Base Cooperative Catalysis. Chem. Eur. J., 17: 12262–12267. doi: 10.1002/chem.201102446

Author Information

  1. 1

    Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan), Fax: (+81) 52-789-5945

  2. 2

    Institute for Advanced Research, Nagoya University, Chikusa, Nagoya 464-8601 (Japan)

  3. 3

    Current Address: Department of Chemistry, Colorado State University (USA)

*Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan), Fax: (+81) 52-789-5945

Publication History

  1. Issue published online: 17 OCT 2011
  2. Article first published online: 21 SEP 2011
  3. Manuscript Received: 6 AUG 2011

Funded by

  • JSPS
  • MEXT

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Keywords:

  • alcohols;
  • alkylation;
  • cooperative catalysis;
  • hydrogen bonds;
  • nucleophilic substitution
Thumbnail image of graphical abstract

Learning to cooperate: A straightforward method for the selective N-mono- and dialkylation of amines with alcohols by means of non-metal-based catalysis promoted by TAPC is reported (see scheme). Selectivity of the N-mono- and dialkylation, substrate scope and functional-group tolerance are highlighted with respect to each amine (1° and 2°; aromatic and aliphatic) and alcohol (1°, 2° and 3°; benzylic and aliphatic) component.

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