Rhodium(III)-Catalyzed Switchable β-C(sp²)–H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3673 - 3678

Published: April 19, 2024

Herein, rhodium(III)-catalyzed β-C(sp2)–H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range substrates typically proceeded with excellent regioselectivity stereoselectivity as well good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized bearing N-(2Z,4E)-butadiene (Z)-β-C(sp2)–H alkylated enamides. In addition, mechanistic experiments suggest that Rh(III)-catalyzed C–H activation is not related critical step.

Language: Английский

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Rhodium(III)-Catalyzed C–C Bond Formation by Direct C–H Activation

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 18, 2025

Abstract Transition-metal-catalyzed functionalizations of C–H bonds to construct C–C represent an ideal route in the synthesis valuable organic molecules. In particular, rhodium(III)-catalyzed bond activation offers attractive strategy due its efficiency and step economy for direct functionalization synthesis. Consequently, recent developments this area have assured a high level regioselectivity reactions. Account, we summarized our achievements sp2- sp3-C–H using rhodium catalyst. The scope, limitation, mechanism these reactions been described briefly. 1 Introduction 2 Arylation 2.1 Aromatic C(sp2)–H 2.2 Benzylic C(sp3)–H 2.3 Olefinic 3 Alkenylation Alkylation 4 Heteroarylation 5 Conclusion

Language: Английский

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Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF₃-Imidoyl Sulfoxonium Ylides via Triple C–H Activation

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 657 - 662

Published: Jan. 7, 2025

A condition-controlled Rh(III)-catalyzed selective synthesis of CF3-substituted indoles and pyrido[2,1-a]isoindoles from 2-arylpyridines CF3-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)3(SbF6)2/HFIP system afforded via triple C–H activation, while the [Cp*RhCl2]2/MeCN condition selectively furnished through [4 + 1] annulation. notable advantages this developed method included readily available starting materials, broad substrate scope, excellent chemoselectivity. Importantly, several selected products showed promising antitumor activities.

Language: Английский

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Base-Mediated Synthesis of Aryl Enol Ethers from α-Aryl Allylic Alcohols and Arylsulfonium Salts

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(38), P. 7866 - 7873

Published: Jan. 1, 2024

A concise synthesis of aryl enol ethers from allylic alcohols and arylsulfonium salts by simply using an inorganic base as a mediator is described. The reaction enabled the facile conversion various α-aryl into corresponding in good yields with excellent selectivity. results demonstrated that both symmetric triarylsulfonium triflate 10-methyl-5-aryl-5,10-dihydrophenothiazin-5-ium were effective arylation reagents for base-initiated selective

Language: Английский

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Non-directed Oxidative Annulation of 2-Arylindazoles with Electron Deficient Olefins via Visible Light Photocatalysis

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10402 - 10405

Published: Jan. 1, 2024

A new visible-light-mediated non-directed oxidative annulation between 2-arylindazoles and electron-deficient olefins using commercially available piperidine-1-sulfonyl chloride as the radical precursor to afford fused 5,6-dihydroindazolo[2,3-

Language: Английский

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Pd(II)‐Catalyzed Formal [5 + 2]‐Carbocyclization of ortho‐Aryl‐Substituted Arylaldehydes with Allylic Alcohols

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 22, 2024

Abstract A Pd(II)‐catalyzed formal [5+2] coupling‐cyclization of 2‐arylbenzaldehydes with allylic alcohols has been developed. The method provides an efficient approach to access diaryl‐fused cycloheptene skeletons via traceless α‐amino acid‐assisted C sp 2 −H activation process.

Language: Английский

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Ru(II)‐Catalyzed C8 Alkenylation of Isoquinolones with Allyl Alcohol

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

Published: Aug. 9, 2024

Abstract A simple Ru(II)‐catalyzed protocol for the alkenylation of isoquinolones with readily accessible allyl alcohols to generate aldehyde bearing has been developed. The use green solvent like dimethyl carbonate makes this method environment‐friendly. Experimental studies were carried out support proposed mechanism. reaction was scaled up showcase application current method.

Language: Английский

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