Oxo-Sulfonylation of 1,7-Enynes via a Multicomponent Oxidative Radical Polar Crossover Approach

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 10, 2025

Diastereoselective synthesis of trans-3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein vinyl carbocation intermediate undergoes nucleophilic substitution to afford corresponding keto functional group. Deprotection N-Ts group, gram-scale synthesis, other synthetic applications were illustrated. Control experiments mechanistic studies show that water acts as nucleophile in this reaction.

Язык: Английский

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Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines

Acta Chimica Sinica, Год журнала: 2024, Номер 82(2), С. 190 - 190

Опубликована: Янв. 1, 2024

Язык: Английский

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Easy Access to Phenanthrenes Through Photoinduced Difunctionalization of Alkynes

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 686 - 686

Опубликована: Янв. 1, 2025

Язык: Английский

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Photocatalytic Regioselective Alkoxycarbonylation/Cyclization of 3-Aza-1,5-dienes: Access to Ester-Containing Pyrrolin-2-ones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 13, 2025

A direct alkoxycarbonyl radical-induced cascade reaction of 3-aza-1,5-dienes with alkyl chlorooxoacetates is reported. With this approach, an extensive range ester-containing pyrrolin-2-ones are synthesized through photocatalyzed alkoxycarbonylation/cyclization under mild conditions. Moreover, dehydrogenative aromatization can proceed the same photocatalytic system.

Язык: Английский

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Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization Reactions of Enediyne in Continuous Flow Conditions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

For the first time, a photoredox-catalyzed alkoxycarbonylation/tricyclization reaction was developed by employing readily accessible enediynes and alkyloxalyl chlorides as starting materials, enabling synthesis of ester-substituted polycyclic N-heteroaromatics under mild conditions through radical-mediated mechanism. This photocatalytic strategy is notable for its exceptional compatibility with diverse functional groups, scalability, efficiency in formation rings chemical bonds. Notably, continuous flow photocatalysis technology markedly improved these reactions compared to equivalent batch reactions, efficiently decreasing times merely 40 min.

Язык: Английский

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Dinuclear-gold-catalyzed cyclization of 1,7-enynes with alkyl bromides

Chemical Communications, Год журнала: 2023, Номер 59(51), С. 7943 - 7946

Опубликована: Янв. 1, 2023

Dinuclear gold-catalyzed radical difunctionalization of alkyl bromides with 1,7-enynes has been established via dehalogenation and 1,5-HAT processes, affording cyclopenta[ c ]quinolines good yields (28 examples, up to 84% yield).

Язык: Английский

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Synthesis of ester-containing phenanthridinesviaphotoredox-catalyzed radical cascade cyclization ofN-arylacrylamides with alkyloxalyl chlorides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 3995 - 4001

Опубликована: Янв. 1, 2023

An alkoxycarbonyl-radical-triggered cascade cyclization reaction of N -( o -cyanobiaryl)acrylamides with alkyloxalyl chlorides is developed, leading to diverse ester-containing phenanthridines.

Язык: Английский

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Photocatalytic, α-Aminoalkyl Radical-Mediated, Methylene-Extrusive Ring-Closing Transformation of o-Alkynyl and o-Cyano Acrylamides

Organic Letters, Год журнала: 2024, Номер 26(17), С. 3652 - 3656

Опубликована: Апрель 24, 2024

Herein we report a visible-light-induced, α-aminoalkyl radical-mediated cascade reaction of 1,7-enynes that establishes unique ring-closing enyne transformation pathway which occurs with concomitant loss methylene moiety. The radical derived from

Язык: Английский

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Alkoxycarbonylation-triggered nitrile insertion/remote C(sp²)–H and C(sp³)–H functionalization to access esterified quinazolinones and amidines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3861 - 3867

Опубликована: Янв. 1, 2024

A new alkoxycarbonyl radical triggered nitrile insertion/remote C(sp 2 )–H and 3 functionalization reaction is developed.

Язык: Английский

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

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6664 - 6669

Опубликована: Июль 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

Язык: Английский

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