Annulation of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(45), P. 6885 - 6888

Published: Jan. 1, 2023

The annulation reactions of enaminones with quinonediimides/quinoneimides for the selective synthesis indoles and 2-aminobenzofurans have been realized. With Zn(II) catalysis, quinonediimides reacted to give via HNMe2-elimination-based aromatization. Fe(III) quinoneimides provided a key dehydrogenative

Language: Английский

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Rh(III)-Catalyzed Redox-Neutral C–H Activation/Annulation of Oxadiazolones with Sulfoxonium Ylides to access oxadiazoloisoquinolinone

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Oxadiazolone-fused isoquinolines were synthesized via Rh( iii )-catalyzed [4+2] annulation and C–H activation, followed by acymethylation products with antidiabetic anti-inflammatory potential.

Language: Английский

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Cobalt(III)-Catalyzed Directed C-7 Selective C–H Alkynylation of Indolines with Bromoalkynes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5411 - 5415

Published: July 17, 2023

A cobalt(III)-catalyzed directed C-7 alkynylation of indolines with easily accessible bromoalkynes has been developed. The reaction a broad substrate scope excellent yields and represents powerful route to the synthesis 7-alkynyl-substituted indolines. In addition, can be extended coupling N-aryl 7-azaindoles, highlighting synthetic practicability strategy.

Language: Английский

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Ruthenium(II)-Catalyzed C–H Activation/Annulation of 5-Phenyl-pyrroline-2-carboxylates with Alkynes: Synthesis of 2,3-Diphenylspiro-[indene-1,2′pyrrolidine]carboxylate Derivatives

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

Published: May 8, 2025

While saturated nitrogen heterocycles are privileged scaffolds, their streamlined catalytic synthesis with unsymmetrical substitution patterns remains a daunting challenge. Herein, we report the ruthenium(II)-catalyzed of spiro[indene-proline] derivatives via C-H activation/annulation 5-phenyl-pyrroline-2-carboxylates alkynes. The protocol utilized imine coordination, resulting in high reaction yields wide range functional group tolerance, scalability, and scaffold diversity. This annulation was successful even various biologically active pharmacophores. featured reversible metalation step suggested possibility base-assisted internal electrophilic pathway.

Language: Английский

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Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(9), P. 985 - 989

Published: Dec. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Language: Английский

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Cobalt-Catalyzed Regioselective C8–H Sulfoxamination of 1-Naphthylamine Derivatives with NH-Sulfoximines

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

Published: Nov. 18, 2024

A simple cobalt-catalyzed, picolinamide-directed C8–H sulfoxamination of 1-naphthalamides with NH-sulfoximines has been developed. This cross-dehydrogenative C–H/N–H coupling reaction offers a facile route to N-arylated sulfoximines, exhibiting high yields, broad substrate scope, and excellent functional group tolerance scalability.

Language: Английский

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Cu(II)-Mediated Sulfonylation of (Hetero)arenes with TosMIC Using Monodentate Directing Groups

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3894 - 3906

Published: Feb. 22, 2024

Monodentate chelation-assisted direct ortho-C–H sulfonylation of (hetero)arenes using TosMIC as the novel sulfonylating reagent has been developed. A broad range substrates, including indolines, indoles, 2-phenylpyridines, and others were well tolerated to afford corresponding products in moderate good yields. Mechanistic studies revealed that sulfonyl radical might be involved. Inspired by above discovery, preliminary para-C–H naphthalene substrate was also successfully realized. The current protocol featured with cheap metal catalysis, functional group compatibility, operational convenience.

Language: Английский

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Rh(III)‐Catalyzed Cross Dehydrogenative Coupling of N‐Phenyl Substituent with Thiophenes

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(19)

Published: April 17, 2023

Abstract Rhodium(III)‐catalyzed cross‐dehydrogenative coupling involves a highly efficient C−C bond formation from N ‐phenyl‐7‐azaindole frameworks, thiophenes. Various novel 7‐azaindole derivatives have been successfully developed with good substrate applicability.

Language: Английский

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Cu-Catalyzed Functionalization of Heterocycles Through C–H Activation

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

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Directing Group Guided Site‐Selective Alkylation of Indoles by Epoxides: Synthesis of β‐Indolylethyl Alcohol Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4416 - 4421

Published: Aug. 7, 2024

Abstract A Palladium catalyzed C4‐ alkylation of indoles using epoxide as an alkylating agent and pivaloyl a weak chelating group has been demonstrated. variety substituted epoxides furnished the desired β‐indolylethyl alcohols in 38%–87% yields. Control experiments indicate that C−H cleavage step is irreversible. The resultant hydroxyl converted to various functional groups demonstrate synthetic utility this protocol.

Language: Английский

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