Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines

Geden, Joanna V.; Pancholi, Alpa K.; Shipman, Michael

doi:10.1021/jo400252n

Cited by 50 publications

(13 citation statements)

References 38 publications

(47 reference statements)

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“…In 2013, Shipman and co-workers reported an efficient three-component reaction to synthesize 2aryl-2-imidazolines, in a palladium mediated catalytic cycle (70) (Scheme 20). [41] The reaction combines aryl halides (67), isocyanides (68), and diamines (69). Initially, different palladium catalysts and ligands were screened with ethylenediamine, tert-butyl isocyanide ( t BuNC), and phenyl iodide (PhI) and the authors identified two combinations of catalyst and ligand, as the most suitable for this reaction.…”

Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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Imidazoline is an important class of compounds found in numerous natural and pharmaceutical products. The compounds are also used as an intermediate in the synthesis of organic molecules. Moreover, chiral imidazolines are widely utilized as organocatalysts to synthesize various natural and synthetic organic compounds. In the past decade, there was an increase in interest in developing new methods to synthesize these imidazoline analogs. Both modification of the previously established methods and the development of new methods are carried out significantly. This review article highlights the progress of the synthesis of imidazoline scaffolds in the last few years (2009-present). The review also described the proposed mechanism illustrated in many of the reports.

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Section: Methods A: Synthesis Of Imidazolines From 12-diaminesmentioning

confidence: 99%

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Mehedi

Tepe

2020

Adv Synth Catal

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“…In 2014, Schipman et al extended the imidoylative Buchwald-Hartwig type cross-coupling to include the use of diamines 57 as coupling partners [43]. This reaction is indicative for imidoylative Buchwald-Hartwig couplings, and proceeds via the oxidative addition of an aryl halide 5 to in situ generated Pd 0 , after which a well-documented 1,1-migratory insertion of the isocyanide can take place.…”

Section: Cross-couplings With Oxygen or Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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“…An efficient palladium‐catalyzed three‐component reaction that combined aryl halides, isocyanides, and 4‐substituted‐ ortho ‐phenylenediamine in the presence of toluene solvent provided access to 5‐substituted‐2‐phenyl‐benzimidazole 28 in 58% yield . The reflux was effected in PdCl 2 (5 mol%) and dppp (10 mol%) as shown in Scheme .…”

Section: Chemistrymentioning

confidence: 99%

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

Ajani

Aderohunmu

Ikpo

et al. 2016

Archiv der Pharmazie

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Benzimidazole derivatives are crucial structural scaffolds found in diverse libraries of biologically active compounds which are therapeutically useful agents in drug discovery and medicinal research. They are structural isosteres of naturally occurring nucleotides, which allows them to interact with the biopolymers of living systems. Hence, there is a need to couple the latest information with the earlier documentations to understand the current status of the benzimidazole nucleus in medicinal chemistry research. This present work unveils the benzimidazole core as a multifunctional nucleus that serves as a resourceful tool of information for synthetic modifications of old existing candidates in order to tackle drug resistance bottlenecks in therapeutic medicine. This manuscript deals with the recent advances in the synthesis of benzimidazole derivatives, the widespread biological activities as well as pharmacokinetic reports. These present them as a toolbox for fighting infectious diseases and also make them excellent candidates for future drug design.

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Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines

Cited by 50 publications

References 38 publications

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

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