Rh-Catalyzed Annulation of Enaminones with Maleimides for Functionalized Aza-spiro α-Tetralones and Benzo[e]isoindoles via C–H Activation/C═C Bond Cleavage

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 142 - 147

Published: Dec. 18, 2023

An unprecedented strategy for Rh-catalyzed C–H activation/C═C bond cleavage of enaminones is described the construction biologically interesting aza-spiro α-tetralones and benzo[e]isoindoles. This protocol provides diversely functionalized benzo[e]isoindoles in good yields via a [4 + 2] annulation exomaleimides maleimides. displays substrate scope, outstanding functional group tolerance, excellent regioselectivity.

Language: Английский

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Rh(III)-catalyzed [4+1] annulation of sulfoxonium ylide with allyl alkyl ethers: A detailed theoretical study of DFT, anti-inflammatory and antidiabetic activity

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(36), P. 15989 - 15999

Published: Jan. 1, 2024

The [4+1] annulation of sulfoxonium ylides with allyl ether, catalyzed by Rh( iii ), efficiently produces alkyl-substituted indanone a broad substrate scope and excellent yield.

Language: Английский

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Rh(III)-catalyzed C–H/C–C activation of benzoylacetonitriles and cyclization with CF3-imidoyl sulfoxonium ylides to 3-trifluoromethyl-isoquinolones

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 427, P. 115098 - 115098

Published: Aug. 19, 2023

Language: Английский

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[Cp*IrCl₂]₂-Catalyzed Amidocarbonation of Olefins with Sulfoxonium Ylides toward Functionalized Isoindolin-1-ones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7148 - 7153

Published: Sept. 26, 2023

A [Cp*IrCl2]2-catalyzed amidocarbonation of olefins with sulfoxonium ylides has been developed to generate diverse biologically important isoindolin-1-ones in high efficiency under mild reaction conditions. Mechanism studies indicated that this cascade was triggered by amino-iridation the olefin unit iridacycle, followed formal migratory insertion ylides. This newly method features broad substrate scopes and operational simplicity.

Language: Английский

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Divergent Synthesis of Dihydrofuran and Dienol Scaffolds via Pd-Catalyzed Decarboxylative Carbene Cross-Coupling

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

Herein, we report a novel ligand-switchable Pd-catalyzed carbene coupling reaction employing vinylethylene carbonates and sulfoxonium ylides. By proper choice of ligands, the chemoselectivity process could be efficiently regulated, allowing for availability dihydrofuran or dienol scaffolds. This method features mild conditions, broad scope, remarkable synthetic utility. Compound 6f can effectively stimulate secretion GLP-1, providing promising insight into development small-molecule agonists GLP-1 receptor.

Language: Английский

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Directed Cascade C–H Functionalization/2-Fold Annulation with Vinylcyclopropanes: Access to Tetrahydrobenzo[g]isochromen-10-ones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 20, 2025

Rh-catalyzed enaminone directed cascade C-H functionalization/2-fold annulation with vinylcyclopropanes has been accomplished to afford functionalized tetrahydrobenzo[g]isochromen-10-ones. The sequential C-H/C-C functionalization, C-C/C-O bond formation, redox-neutral conditions, functional group tolerance, and late-stage modification of the natural products are important practical features.

Language: Английский

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Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4595 - 4602

Published: Nov. 1, 2023

Abstract A substrate‐controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)‐catalyzed C−H bond activation is developed. The reaction 2‐methyl‐ N ‐arylmaleimides in the presence AgNTf 2 diastereoselectively provides diversely functionalized indanonylpyrroline‐2,5‐dione derivatives. Furthermore, AgBF 4 , subsequent leads to biologically intriguing various spiroindanonylpyrroline‐2,5‐diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.

Language: Английский

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Pragmatic Access to Hybrid Quinoxaline Scaffold Mediated by Elemental Sulfur Enabling Actualization to π-Extended and Aza-Annulated Heterocyclic Units

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A metal-free approach for synthesizing hybrid quinoxaline derivatives from sulfoxonium ylide and a 1,5-bis-nucleophilic N-heterocycle mediated by elemental sulfur is presented to illuminate the [5+1] cascade cyclization sequence. Large-scale synthesis postsynthetic functionalizations annulative π-extension intramolecular aza-annulation reactions reveal potential utility actualize fabricated approach.

Language: Английский

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Expedient C–H allylation of sulfoxonium ylides: merging C–H and C–C/C–het bond activation

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(95), P. 14173 - 14176

Published: Jan. 1, 2023

Sulfoxonium ylide chelation-assisted C-H allylation of arenes has been accomplished utilizing strained vinyl carbo/heterocycles as the allyl surrogates via sequential and C-C/het bond activation. Broad substrate scope, Co-catalysis, selectivity, late-stage drug mutation are important practical features.

Language: Английский

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Synthesis and structure of unsymmetrical 1,1′-disubstituted cyclopropane-containing azinylferrocenes

Russian Chemical Bulletin, Journal Year: 2023, Volume and Issue: 72(12), P. 2815 - 2824

Published: Dec. 1, 2023

Language: Английский

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