HAT‐Mediated Electrochemical C(sp2)−H Alkoxylation of Pyrido[1,2‐a]pyrimidin‐4‐ones with Aliphatic Alcohols DOI
Subhadeep Ghosh, Sumit Biswas, Indrajit Das

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract A direct alkoxylation of the electron‐deficient olefinic C(sp 2 )−H bond in pyrido[1,2‐ a ]pyrimidin‐4‐ones using aliphatic alcohols has been developed under transition metal and external chemical oxidant‐free electrochemical conditions. Azidotrimethylsilane (TMSN 3 ) is utilized as hydrogen atom transfer (HAT) reagent to enable homolytic cleavage unfunctionalized O−H alcohols, thereby generating electrophilic alkoxy radicals. Moreover, effectiveness this method demonstrated with d 4 ‐methanol (CD OD), leading synthesis ‐methoxylated N ‐heterocycles good yields sustainable The proposed mechanism, based on or trideuteromethoxy radicals, substantiated by control experiments cyclic voltammetry (CV) studies.

Language: Английский

HAT‐Mediated Electrochemical C(sp2)−H Alkoxylation of Pyrido[1,2‐a]pyrimidin‐4‐ones with Aliphatic Alcohols DOI
Subhadeep Ghosh, Sumit Biswas, Indrajit Das

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract A direct alkoxylation of the electron‐deficient olefinic C(sp 2 )−H bond in pyrido[1,2‐ a ]pyrimidin‐4‐ones using aliphatic alcohols has been developed under transition metal and external chemical oxidant‐free electrochemical conditions. Azidotrimethylsilane (TMSN 3 ) is utilized as hydrogen atom transfer (HAT) reagent to enable homolytic cleavage unfunctionalized O−H alcohols, thereby generating electrophilic alkoxy radicals. Moreover, effectiveness this method demonstrated with d 4 ‐methanol (CD OD), leading synthesis ‐methoxylated N ‐heterocycles good yields sustainable The proposed mechanism, based on or trideuteromethoxy radicals, substantiated by control experiments cyclic voltammetry (CV) studies.

Language: Английский

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