Synthesis of Fused or Spiro Polyheterocyclic Compounds via the Dehydrogenative Annulation Reactions of 2-Arylindazoles with Maleimides

Organic Letters, Journal Year: 2019, Volume and Issue: 21(18), P. 7189 - 7193

Published: Sept. 4, 2019

A dehydrogenative annulation of 2-arylindazoles with maleimides for the switchable synthesis indazolo[2,3-a]pyrrolo[3,4-c]quinolinones or spiroindolo[1,2-b]indazole-11,3′-pyrrolidinones is presented. Mechanistically, formation title compounds involves a Rh(III)-catalyzed C–H metalation 2-arylindazole, followed by maleimide insertion and intramolecular cyclization. Interestingly, selectivity to form fused spiro could be switched resorting different additives. The notable features this protocol include simple substrates excellent atom economy regioselectivity.

Language: Английский

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Traceless directing groups: a novel strategy in regiodivergent C–H functionalization

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(83), P. 12479 - 12521

Published: Jan. 1, 2020

The use of functional groups as internal ligands for assisting C-H functionalization, termed the chelation assisted strategy, is emerging one most powerful tools construction C-C and C-X bonds from inert bonds. However, there are various directing which cannot be either removed after functionalization or require some additional steps reagents their removal, thereby limiting scope structural diversity products, step atom economy system. These limitations overcome by traceless group (TDG) strategy wherein substrate removal can carried out in a pot fashion. Traceless serve ideal with high degree reactivity selectivity without any requirement removal. present review overviews such carboxylic acids, aldehydes, N-oxides, nitrones, N-nitroso amines, amides, sulfoxonium ylides silicon tethered transition metal catalyzed reactions last decade.

Language: Английский

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Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(12), P. 1527 - 1569

Published: Jan. 1, 2020

Heterocyclic alkenes and their derivatives are an important class of reactive feedstock valuable synthons. This review highlights the transition-metal-catalyzed coupling heterocyclic alkenesviaa C–H functionalization strategy.

Language: Английский

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Synthesis of Chiral Spirolactams via Sequential C−H Olefination/Asymmetric [4+1] Spirocyclization under a Simple Co^II/Chiral Spiro Phosphoric Acid Binary System

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(43), P. 23187 - 23192

Published: Aug. 26, 2021

Abstract An unprecedented enantioselective synthesis of spiro‐γ‐lactams via a sequential C−H olefination/asymmetric [4+1] spirocyclization under simple Co II /chiral spiro phosphoric acid (SPA) binary system is reported. A range biologically important are obtained with high levels enantioselectivity (up to 98 % ee ). The concise, asymmetric an aldose reductase inhibitor was successfully achieved. Notably, contrast previous reports that relied on the use cyclopentadienyl or its derivatives (achiral Cp*, Cp tBu , chiral x ) ligated III complexes requiring tedious steps prepare, cheap and commercially available cobalt(II) acetate tetrahydrate used as efficient precatalyst.

Language: Английский

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Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 2916 - 2947

Published: Jan. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Language: Английский

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Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1535 - 1541

Published: Feb. 3, 2020

Maleimide is widely applied in many fields, especially antibody–drug conjugations and peptide drugs. Herein, we develop a strategy for the C–H alkenylation of tryptophan tryptophan-containing peptides, providing synthetic route decorating maleimide on peptides. The method has high tolerance functional groups protecting groups. Furthermore, this was to prepare conjugation with molecules such as drugs fluorescence probes. Moreover, macrocyclic peptides were obtained via reaction.

Language: Английский

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Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(24), P. 4837 - 4845

Published: Jan. 1, 2022

Transition-metal-catalyzed directed C-H alkenylation with maleimides has attracted much attention in recent years, as maleimide core moieties are present various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important compounds including succinimides, pyrrolidines γ-lactams. The efficient chelation-assisted inert bond activation strategy provides straightforward access to a wide array of structurally diverse molecules containing units. This review describes the major progress mechanistic investigations on Heck-type reaction/cyclization organic until early 2022.

Language: Английский

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Stereoselective C(sp²)–H Alkylation of Enamides with Unactivated Aliphatic Carboxylic Acids via Decarboxylative Cross-Coupling Reactions

Organic Letters, Journal Year: 2019, Volume and Issue: 21(20), P. 8395 - 8399

Published: Oct. 3, 2019

An efficient and straightforward stereoselective alkylation reaction of enamides using commercially available easily accessible unactivated alkyl carboxylic acids as alkylating agents is described, giving rise to a diverse array synthetically important geometrically defined β-alkylated bearing primary, secondary, or tertiary moieties. This transformation also shows excellent functional group tolerance, satisfying atom economy, operational simplicity.

Language: Английский

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Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(43), P. 5862 - 5879

Published: Oct. 20, 2021

Abstract Maleimides and succinimides are all vital scaffolds in biological fields various natural products. Maleimide derivatives have been extensively used as coupling partners for organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, variety efficient chelation‐assisted strategies employed selective addition C−H bonds to maleimides giving succinimides, which also highly building blocks synthesis. This Review provides an overview research progress relating participated transition‐metal‐catalyzed group‐directed alkylation from 2012 2021. Significant advances this field were highlighted, diverse transition metal catalysts, substrates contained different directing groups, reaction mechanisms well synthetic applications systematically discussed. addition, limitations intractable issues need be solved future pointed out.

Language: Английский

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Rh(III)-Catalyzed [4 + 2] Annulation of 3-Aryl-5-isoxazolone with Maleimides or Maleic Ester

Organic Letters, Journal Year: 2020, Volume and Issue: 22(16), P. 6484 - 6488

Published: Aug. 12, 2020

The Rh(III)-catalyzed [4 + 2] annulation of 3-aryl-5-isoxazolones with maleimides or maleic ester has been developed, which gives synthetically important 3,4-dihydroisoquinoline derivatives in good to excellent yields. This facile protocol can tolerate a variety functional groups, and CO2 was produced as the predominant byproduct. Notably, C-C bond C-N were formed simultaneously. could be easily scaled up.

Language: Английский

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