Mechanisms, regio- and stereoselectivities involved in NHC catalyzed dearomatizing annulation of ester with ylide: A computational study

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 560, P. 114146 - 114146

Published: April 16, 2024

Language: Английский

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Oxidative N-Heterocyclic Carbene-Catalyzed Intramolecular Friedel–Crafts Alkylation of Indoles for the Synthesis of Spirocyclic Indolenines

Organic Letters, Journal Year: 2022, Volume and Issue: 24(29), P. 5314 - 5318

Published: July 14, 2022

The stereoselective intramolecular dearomatizing spirocyclization of indoles via oxidative N-heterocyclic carbene (NHC) catalysis to afford indolenines bearing an all-carbon quaternary center at the 3-position is reported. reaction proceeds nucleophilic addition indole in situ generated α,β-unsaturated acyl azolium. cyclized indolenine azolium functionality trapped by a suitable external nucleophile that does not efficiently react with direct acylation.

Language: Английский

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Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10816 - 10830

Published: July 15, 2024

Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β'-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed gives benzothiazole-fused 1,4-dihydropyridine carboxylates (3 + 3) chemoselectively. By contrast, PR

Language: Английский

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Bifunctional Squaramide-Catalyzed Asymmetric Cascade Reaction of Benzothiazoles with 2-Nitroallylic Acetates or Nitroenynes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9164 - 9169

Published: Dec. 14, 2023

We describe here an organocatalytic asymmetric cascade formal [3 + 3] cycloaddition of benzothiazoles with 2-nitroallylic acetates and nitroenynes. This dearomative methodology provided a facile efficient strategy for the construction broad range valuable benzothiazolopyridines bearing two adjacent stereogenic centers in moderate to good yields excellent stereocontrol.

Language: Английский

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Asymmetric Substitution by Alkynyl Copper Driven Dearomatization and Rearomatization

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(47)

Published: Oct. 16, 2023

Abstract Catalytic asymmetric transformations by dearomatization have developed into a widely applicable synthetic strategy, but heavily relied on the use of arenes bearing heteroatom. In this case, is facilitated involvement p ‐orbital electron Different from conventional substrate‐dependent model, here we demonstrate that activation d transition‐metal center can serve as driving force for dearomatization, and applied to development novel alkynyl copper remote substitution reaction. A newly modified PyBox chiral ligand enables construction valuable diarylmethyl triarylmethyl skeletons in high enantioselectivities. An unexpected tandem process involving sequential substitution/cyclization/1,5‐H shift leads formation enantioenriched C−N axis. gram‐scale reaction various downstream highlight robustness method potential products. Preliminary mechanistic studies reveal mononuclear Cu‐catalyzed process.

Language: Английский

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Dual visible-light and NHC-catalyzed radical relay trifunctionalization of unactivated alkenes

Chemical Synthesis, Journal Year: 2023, Volume and Issue: 3(4)

Published: Nov. 17, 2023

Radical trifunctionalization of unactivated alkenes remains rare and challenging, although they can provide a robust tool for the construction molecules with high added value from simple materials. This work presents relay dual N-heterocyclic carbene organocatalytic visible-light photocatalytic multi-component alkyl via merger remote 1,4-cyano migration alkylacylation. The method features broad substrate scope good compatibility diverse functional groups. Density theory calculations were also carried out to rationalize origin this reaction. cooperative photoredox catalysis enabled reductive single-electron transfer reaction acyl azolium species subsequent radical-radical cross-coupling, allowing facile three new C−C bonds in one-pot reactions regioselectivity.

Language: Английский

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Asymmetric Brominative Dearomatization of 2-Naphthols Using a Cinchona Alkaloid-Based Organocatalyst

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4232 - 4236

Published: March 4, 2024

A cinchona alkaloid-based organocatalyst enables asymmetric brominative dearomatization of 2-naphthols, providing the corresponding bromonaphthalenones with high enantioselectivities. The first metal-free reaction can accommodate a variety functional groups and give useful frameworks bearing Br-containing tetrasubstituted stereogenic center.

Language: Английский

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Greener Synthetic Strategies for Azepinones

Organic Preparations and Procedures International, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 29

Published: Dec. 17, 2024

Language: Английский

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N-heterocyclic carbenes/Palladium Synergistic Catalysis in Organic Synthesis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4613 - 4624

Published: Jan. 1, 2024

This review summarizes the progress made in area of synergistic catalysis with N-heterocyclic carbenes and palladium.

Language: Английский

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N-Heterocyclic Carbene Catalyzed the Umpolung of Aldehyde Compounds

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2204 - 2204

Published: Jan. 1, 2024

Language: Английский

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