Chomphunuch T.La-ongthong K.Katrun P.Sawektreeratana N.Keawkla N.Soorukram D.Leowanawat P.Reutrakul V.Surawatanawong P.Bunchuay T.Kuhakarn C.Mahidol University2025-01-262025-01-262025-01-01Chemistry - An Asian Journal (2025)18614728https://repository.li.mahidol.ac.th/handle/20.500.14594/103042Described herein is a facile electrochemical strategy for the generation of formaldehyde from N,N-dimethylacetamide (DMA) and water (H2O) toward a direct and site-selective N-hydroxymethylation of indoles and derivatives. Mechanistic studies suggested that N-(hydroxymethyl)-N-methylacetamide generated in situ from DMA/H2O under electrochemical conditions serves as a formaldehyde surrogate. The developed methodology features mild, base- and metal catalyst-free conditions. The reaction can accommodate a broad range of substrate scopes and offers an alternative route to access a series of N-hydroxymethylated indole, bis-indole, carbazole, and indazole derivatives. A gram-scale synthesis was demonstrated to show the scaled-up applicability of this transformation.ChemistryBiochemistry, Genetics and Molecular BiologyArticleSCOPUS10.1002/asia.2024014892-s2.0-852155101561861471X