Visible-Light-Induced Cascade Cyclization of 1-(2-(Arylethynyl)benzoyl)indoles into Sulfonated Benazepino[1,2-a]indolones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(50), P. 10982 - 10987

Published: Dec. 10, 2024

1-(2-(Arylethynyl)benzoyl)indoles were developed as an innovative scaffold for radical cascade cyclization under visible-light and mild conditions, enabling efficient synthesis of sulfonated benazepino[1,2-

Language: Английский

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Rapid Access to γ,γ‐Dichloroketones via Radical‐Induced Dichloromethylation and Concomitant 1,2‐Aryl Migration of Allylic Alcohols with CHCl₃

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3843 - 3848

Published: Oct. 10, 2023

Abstract A radical‐induced dichloromethylation and concomitant 1,2‐aryl migration of allylic alcohols with CHCl 3 is developed for the construction γ,γ‐dichloroketones in moderate to good yields. We found that, para ‐substituted unsymmetrical substrates, more electron‐deficient aryl group migrates preferentially over electron‐rich group. Moreover, chlorocyclopropanes could be obtained from allyl one‐pot manner through radical‐addition/1,2‐aryl migration/nucleophilic substitution.

Language: Английский

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Synergistic Merger of Ketone, Halogen Atom Transfer (XAT), and Nickel-Mediated C(sp³)–C(sp²) Cross-Electrophile Coupling Enabled by Light

ACS Organic & Inorganic Au, Journal Year: 2023, Volume and Issue: 4(2), P. 229 - 234

Published: Dec. 12, 2023

In the present manuscript, we have developed a unique catalytic system by merging photoexcited ketone catalysis, halogen atom transfer (XAT), and nickel catalysis to forge C(sp3)–C(sp2) cross-electrophile coupling products from unactivated iodoalkanes (hetero)aryl bromides. The synergistic works under mild reaction conditions tolerates variety of functional groups; moreover, this strategy allows late-stage modification medicinally relevant molecules. Preliminary mechanistic studies reveal role α-aminoalkyl radical, which further participates in XAT process with alkyl iodides generate desired eventually intercepts cycle liberate good excellent yields.

Language: Английский

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Direct C(sp²)–H fluoroalkylation of quinoxalin-2(1H)-ones with (fluoroalkyl)triphenylphosphonium salts and alkenes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5375 - 5382

Published: Jan. 1, 2023

A photoredox-catalyzed direct C(sp 2 )–H fluoroalkylation of quinoxalin-2(1 H )-ones with (fluoroalkyl)triphenylphosphonium salts and alkenes is described, providing a practical approach for the generation diverse fluoroalkyl-containing )-ones.

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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