Photocatalytic N‑Methylation of Amines over Pd/TiO2 for the Functionalization of Heterocycles and Pharmaceutical Intermediates
ACS Sustainable Chemistry & Engineering
American Chemical Society (ACS)
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Wheatley, A., Wang, L., Binder, 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
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.
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.).
External DOI: https://doi.org/10.1021/acssuschemeng.8b03855
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285822