Rh(III)‐Catalyzed [4+2] Cyclization of 2‐Aryl‐1<i>H</i>‐benzo[<i>d</i>]imidazoles with Maleimides via C‐H Activation

Deng, Chen; Li, Changchang; Yao, Jinzhong; Jin, Quanli; Miao, Maozhong; Zhou, Hongwei

doi:10.1002/ejoc.202100612

Cited by 15 publications

(2 citation statements)

References 56 publications

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“…[31] Acidic additives such as PivOH and adamantanecarboxylic acid (ADA) proved to be fruitful in improving the In comparison to Fan and Zhang's work, [25a] Miao and Yao reported the rhodium-catalyzed [4 + 2]-cyclization reactions of 2-aryl-1H-benzo[d] imidazoles with maleimides through sequential activation of NÀ H and CÀ H bonds, yielding a series of nitrogen-containing cis-dihydrobenzimidazo[2,1-a]isoquinolines (Scheme 26). [32] Besides, 2-aryl-1H-phenanthro [9,10-d]imidazoles could also be applied to the synthesis of phenanthroimidazoles bearing heterocyclic spacers under the optimized conditions.…”

Section: Rhodiummentioning

confidence: 99%

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

et al. 2021

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

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Section: Rhodiummentioning

confidence: 99%

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

et al. 2021

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“…Maleimides have been identified as powerful two-carbon electrophilic coupling partners in transition-metal-catalyzed annulation reactions due to their convenient accessibility and unique reactivity . However, coupling of maleimides with 2-alkenyl/2-arylimidazoles has only been studied using Rh(III) catalysts . For example, Lee et al described Rh(III)-catalyzed annulation of 2-arylbenzimidazoles with maleimides where depending upon the reaction conditions two structurally distinct succinimide-bearing benzimidazole-fused isoquinoline derivatives were obtained .…”

Section: Introductionmentioning

confidence: 99%

Ru(II)-Catalyzed [4 + 2]-Annulation of 2-Alkenyl/Arylimidazoles with N-Substituted Maleimides and 1,4-Naphthoquinones: Access to Imidazo-Fused Polyheterocycles

Meena,

Nipate,

Swami

et al. 2024

J. Org. Chem.

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Synthesis of imidazo-fused polyheterocyclic molecular frameworks, viz. imidazo[1,2-a]pyrrolo[3,4-e]pyridines, imidazo[2,1a]pyrrolo[3,4-c]isoquinolines, and benzo[g]imidazo[1,2-a]quinoline-6,11-diones, has been achieved by the ruthenium(II)-catalyzed [4 + 2] C−H/N−H annulation of 2-alkenyl/2-arylimidazoles with Nsubstituted maleimides and 1,4-naphthoquinones. The developed protocol is operationally simple, exhibits broad substrate scope with excellent functional group tolerance, and provides the desired products in moderate to good yields. The mechanistic studies suggest that the reaction involves the formation of a C−C bond through Ru-catalyzed C(sp 2 )−H bond activation followed by intramolecular cyclization.

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Rhodium‐Catalyzed CH Functionalization to Construct Annulated Molecules

Mahato

Sarkar

Naskar

et al. 2022

Handbook of CH-Functionalization

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Rhodium complexes are exceptionally significant in homogeneous catalysis. The synthetic community observed the rapid burgeoning of such rhodium catalysis since the discovery of Wilkinson's catalyst. Rhodium‐catalyzed tandem C(sp 2 )H/C(sp 3 )H activation and annulation with alkenes, alkynes, arenes, and other reactive partners is a rapidly growing research field to obtain a new class of heterocycles and thereby generates potential biologically active pharmacophores. Superior reactivity of rhodium catalysts is attributed due to its good π‐acceptor character that favors the CH bond activation reaction of substrates containing a wide range of directing groups, such as amides, imines, carboxylic acid (derivatives), benzylic alcohols, ketones, various heterocycles and shown efficiency toward annulation reaction with various befitting partners; even undirected CH activations have also been achieved. This article provides a brief account of the recent developments in rhodium‐catalyzed CH activation/annulation reactions for the synthesis of new classes of fused cyclic scaffolds using suitable coupling partners. For the rhodium‐catalyzed annulation strategies, different types of cyclization reactions, namely, oxidative, redox‐neutral, photoredox, electrochemical reactions are discussed. In addition, the enantioselective synthesis of annulated molecules using chiral rhodium catalysts has also been highlighted.

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Rh(III)‐Catalyzed [4+2] Cyclization of 2‐Aryl‐1H‐benzo[d]imidazoles with Maleimides via C‐H Activation

Cited by 15 publications

References 56 publications

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

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

Ru(II)-Catalyzed [4 + 2]-Annulation of 2-Alkenyl/Arylimidazoles with N-Substituted Maleimides and 1,4-Naphthoquinones: Access to Imidazo-Fused Polyheterocycles

Rhodium‐Catalyzed CH Functionalization to Construct Annulated Molecules

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