Visible Light-Induced Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings DOI

Vadla Shiva Prasad,

Silari Mohana Krishna,

Vadithya Ranga Rao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

The direct alkylation of carbonyl compounds at α & β positions represents a significant challenge. Here, we report catalyst-free visible light-induced deaminative that efficiently produces α, β-alkylated malononitrile-assisted ketones. Mechanistic studies suggested an EDA complex is formed by the Katritzky salt and carbanion malononitrile-aided ketones, which permits disruption C-N bonds generation alkyl radicals. Remarkably, this strategy eliminates need for metal catalysts, additives, ligands offering enhanced environmental sustainability features mild, catalyst-free, broad functional group tolerance. Our optimized condition under blue LED light yielded regio isomers ketones in good to excellent yields with diverse electronic properties substitutions. Implementation flow setup batch protocol efficiency reaction, demonstrating robustness organic synthesis.

Language: Английский

Visible Light-Induced Alkylation of Malononitrile-Assisted Ketones through Deaminative Couplings DOI

Vadla Shiva Prasad,

Silari Mohana Krishna,

Vadithya Ranga Rao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

The direct alkylation of carbonyl compounds at α & β positions represents a significant challenge. Here, we report catalyst-free visible light-induced deaminative that efficiently produces α, β-alkylated malononitrile-assisted ketones. Mechanistic studies suggested an EDA complex is formed by the Katritzky salt and carbanion malononitrile-aided ketones, which permits disruption C-N bonds generation alkyl radicals. Remarkably, this strategy eliminates need for metal catalysts, additives, ligands offering enhanced environmental sustainability features mild, catalyst-free, broad functional group tolerance. Our optimized condition under blue LED light yielded regio isomers ketones in good to excellent yields with diverse electronic properties substitutions. Implementation flow setup batch protocol efficiency reaction, demonstrating robustness organic synthesis.

Language: Английский

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