Photochemical Divergent Ring-Closing Metathesis of 1,7-Enynes: Efficient Synthesis of Spirocyclic Quinolin-2-ones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6664 - 6669

Published: July 30, 2024

A photocatalytic method for the ring-closing 1,7-enyne metathesis using α-amino radical as an alkene deconstruction auxiliary is present. Preliminary mechanistic studies suggest that intramolecular 1,5-hydrogen atom transfer key to generation and β-scission of radical, while dearomatization arenes ring opening cyclopropanes are construct spirocyclic quinolin-2-ones. This approach highlights potential metathesis, providing a green, efficient, step-economical way synthesis

Language: Английский

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Synthesis of Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13641 - 13653

Published: Sept. 5, 2024

We report a visible light-induced photoreductive strategy for three-component diarylation of alkenes with aryl halides and cyanoaromatics. Upon photoredox catalysis tertiary alkyl amines as the electron transfer agent, selectively undergo halogen atom to generate radicals two C(sp

Language: Английский

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Photoredox-Catalyzed Three-Component 1,2-Cyanoalkylpyridylation of Styrenes with Nonredox-Active Cyclic Oximes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16410 - 16423

Published: Nov. 9, 2023

Three-component alkene 1,2-difunctionalizations have emerged as a powerful strategy for rapid buildup of diverse and complex alkylpyridines, but the distal functionalized alkyl radicals 1,2-alkylpyridylations were still rare. Herein, we report an example regioselective three-component 1,2-cyanoalkylpyridylation feedstock styrenes with accessible nonredox-active cyclic oximes through visible-light photoredox catalysis, providing series structurally β-cyanoalkylated alkylpyridines. This protocol proceeds radical relay pathway including generation iminyl enabled by phosphoranyl radical-mediated β-scission, transposition C-C bond cleavage, highly selective addition, precise radical-radical cross-coupling sequence, thus facilitating formation two distinct single bonds in single-pot operation. synthetic features mild conditions, broad compatibility functional groups substrate scope, product derivatization, late-stage modification.

Language: Английский

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Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 940 - 940

Published: Jan. 1, 2024

Language: Английский

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Iron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 18, 2024

A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl undergo halogen atom transfer methyl radicals to form in reactions initiated by a combination

Language: Английский

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