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Org Lett. 2015 May 15;17(10):2530-3. doi: 10.1021/acs.orglett.5b01063. Epub 2015 Apr 27.

N-methylation of amines with methanol at room temperature.

Organic letters

Vasily N Tsarev, Yuna Morioka, Joaquim Caner, Qing Wang, Richiro Ushimaru, Akihiko Kudo, Hiroshi Naka, Susumu Saito

Affiliations

  1. †Research Center for Materials Science and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
  2. ‡Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjyuku, Tokyo 162-8601, Japan.
  3. §Institute for Advanced Research, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
  4. ?JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa, Tokyo 141-0021, Japan.

PMID: 25915546 DOI: 10.1021/acs.orglett.5b01063

Abstract

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups.

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