Electro-oxidative Methylation of 2-Isocyanobiaryls Using N,N-dimethylformamide (DMF) as Carbon Source: Synthesis of 6-Methylphenanthridines.

Autor: La-Ongthong K; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand., Chantarojsiri T; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand., Soorukram D; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand., Leowanawat P; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand., Reutrakul V; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand., Kuhakarn C; Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2024 May 02; Vol. 19 (9), pp. e202400176. Date of Electronic Publication: 2024 Apr 10.
DOI: 10.1002/asia.202400176
Abstrakt: A benign electrochemical method to access 6-methylphenanthridines from 2-isocyanobiaryls using N,N-dimethylformamide (DMF) as a methyl source is reported. The protocol operates at ambient temperature without the need for harmful methylating reagents. Mechanistic studies suggested that DMF delivered a methylene synthon, followed by reduction at the cathode and tautomerization. The method offers environmental benefits by avoiding metal-based reagents and harsh conditions.
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Databáze: MEDLINE
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