N-methylation of amines with methanol at room temperature

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

doi:10.1021/acs.orglett.5b01063

N-methylation of amines with methanol at room temperature

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

Authors

Vasily N Tsarev¹, Yuna Morioka¹, Joaquim Caner¹, Qing Wang¹, Richiro Ushimaru¹, Akihiko Kudo², Hiroshi Naka¹, Susumu Saito^{1

3

4}

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.