{"title":"Electrochemically Driven Site-Selective N-Hydroxymethylation of Indoles and Derivatives.","authors":"Thanathip Chomphunuch, Kannika La-Ongthong, Praewpan Katrun, Natthapat Sawektreeratana, Natchayatorn Keawkla, Darunee Soorukram, Pawaret Leowanawat, Vichai Reutrakul, Panida Surawatanawong, Thanthapatra Bunchuay, Chutima Kuhakarn","doi":"10.1002/asia.202401489","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202401489"},"PeriodicalIF":3.5000,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202401489","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Electrochemically Driven Site-Selective N-Hydroxymethylation of Indoles and Derivatives.
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.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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