Electrochemically Driven Site-Selective N-Hydroxymethylation of Indoles and Derivatives
Issued Date
2025-01-01
Resource Type
ISSN
18614728
eISSN
1861471X
Scopus ID
2-s2.0-85215510156
Journal Title
Chemistry - An Asian Journal
Rights Holder(s)
SCOPUS
Bibliographic Citation
Chemistry - An Asian Journal (2025)
Suggested Citation
Chomphunuch T., La-ongthong K., Katrun P., Sawektreeratana N., Keawkla N., Soorukram D., Leowanawat P., Reutrakul V., Surawatanawong P., Bunchuay T., Kuhakarn C. Electrochemically Driven Site-Selective N-Hydroxymethylation of Indoles and Derivatives. Chemistry - An Asian Journal (2025). doi:10.1002/asia.202401489 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/103042
Title
Electrochemically Driven Site-Selective N-Hydroxymethylation of Indoles and Derivatives
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Abstract
Described 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.