Synergistic Brønsted Base/Photoredox‐Catalyzed Three‐Component Coupling with Malonates to Synthesize δ‐Hydroxy Esters and δ‐Keto Esters

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(9), P. 957 - 962

Published: Jan. 18, 2024

Comprehensive Summary Multicomponent alkene 1,2‐dicarbofunctionalizations (DCFs) have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C—C double bond in step for enhancing molecular complexity and diversity. To the best of our knowledge, there is only report on photoredox‐catalyzed three‐component DCFs with malonates through radical−radical cross‐coupling, while radical‐polar crossover (RPC)‐type were still rare. Herein, we describe redox‐neutral RPC‐type 1,2‐dialkylation styrenes aldehydes synergistic Brønsted base/photoredox catalysis system. This transition‐metal‐free provides an efficient clean approach broad variety δ‐hydroxy esters also features exceptionally mild conditions, wide compatibility substrate scope functional groups, high atomic economy. Moreover, 1,2‐alkylacylation from same starting materials was achieved one‐pot manner such coupling subsequent two‐electron oxidation process, providing set δ‐keto interest pharmaceutical research.

Language: Английский

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Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines

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

Published: March 3, 2025

We report the photocatalyzed three-component alkene 1,2-alkylpyridylation reaction between alkylboronic acids, 4-cyanopyridine, and an olefin to achieve pyridination alkylation of synthesis structurally diversified 4-alkylpyridines. The readily available easily manipulated acids were used as alkyl radical precursors. reactions take place under mild conditions with a broad substrate scope are easy scale up gram level, they therefore potential practical value for structural modification biologically active alkylpyridine derivatives.

Language: Английский

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Hybrid Heterocycles: Ag(I)-Catalyzed C–C/C–N/C–O Coupled Cascade Dual Cyclization to Valuable Indolo-4H-indolones and Indolo-4H-chromenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2556 - 2570

Published: Jan. 26, 2024

Herein, we report a highly efficient Ag(I)-catalyzed indolyzation with Friedel–Crafts alkylation through cascade cyclization strategy for accessing valuable hybrid heterocycles the first time. This general consists of forming four C–C/C–N/C–O bonds toward dual annulation reactions 2-alkynylanilines methyl benzoate-2-carboxaldehydes and aromatic amines, as well salicylaldehydes malononitrile. Variably substituted new indolo-4H-phthalimidines indolo-4H-chromenes were synthesized excellent yields (85–93%) under mild reaction conditions.

Language: Английский

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Visible-Light-Induced alkyl-arylation of olefins via a Halogen-Atom Transfer Process

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6370 - 6375

Published: Jan. 1, 2024

Visible-light-induced three-component 1,2-alkyl-arylation of alkenes and alkyl radical addition/cyclization acrylamides have been realized using a photocatalytic halogen-atom transfer (XAT) strategy.

Language: Английский

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