Photocatalytic N‑Methylation of Amines over Pd/TiO2 for the Functionalization of Heterocycles and Pharmaceutical Intermediates
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Publication Date
2018Journal Title
ACS Sustainable Chemistry & Engineering
ISSN
2168-0485
Publisher
American Chemical Society (ACS)
Type
Article
Metadata
Show full item recordCitation
Wheatley, A., Wang, L., Jenkinson, K., Kuwata, K., Saito, S., & Naka, H. (2018). Photocatalytic N‑Methylation of Amines over Pd/TiO2 for the Functionalization of Heterocycles and Pharmaceutical Intermediates. ACS Sustainable Chemistry & Engineering https://doi.org/10.1021/acssuschemeng.8b03855
Abstract
Amines in heteroaromatic systems and pharmaceutical intermediates were functionalized through N-methylation with methanol using a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. This method provides access to a series of tertiary N-methylamines bearing N-, O-, and/or S-containing heteroaromatic functionalities from primary/secondary amines and methanol under mild reaction conditions. Facile syntheses of several pharmaceuticals containing N-methyl or ethyl groups, as well as related deuterated drugs, was achieved through the late-stage functionalization of amines.
Keywords
Green chemistry, Photocatalysis, Methylation, Methanol, Pharmaceuticals
Relationships
Sponsorship
This work was supported by JSPS KAKENHI Grant Number
JP26410115 (H.N.), the Tobe Maki Scholarship Foundation
(H.N.), the JGC-S Scholarship Foundation (H.N.), Fusion Emergent
Research Program from Integrated Research Consortium on
Chemical Sciences (IRCCS, H.N. and A.E.H.W.), the JST ACT-C
program (S.S.), and the UK EPSRC (EP/J500380/1, K.J.).
Identifiers
External DOI: https://doi.org/10.1021/acssuschemeng.8b03855
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285822
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