Cobalt‐Catalyzed Aerobic Oxidative Cyclization of 2‐Aminoanilines with Isonitriles: Facile Access to 2‐Aminobenzimidazoles

Liu, Jiaqi; Morgan, Sarah E.; Hoover, Jessica M.

doi:10.1002/cctc.201902011

Cited by 5 publications

(3 citation statements)

References 53 publications

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“…Liu et al designed a protocol to access 2-aminobenzimidazoles from 2-aminoanilines and isonitriles. 176 The cobalt-catalyzed synthesis delivered 2-aminobenzimidazoles in modest to excellent yields ( Scheme 107 ).…”

Section: Benzimidazole Synthesis By Condensation Of 12-benzenediamine...mentioning

confidence: 99%

Recent achievements in the synthesis of benzimidazole derivatives

Chung,

Dung,

Duc

2023

RSC Adv.

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Section: Benzimidazole Synthesis By Condensation Of 12-benzenediamine...mentioning

confidence: 99%

Recent achievements in the synthesis of benzimidazole derivatives

Chung,

Dung,

Duc

2023

RSC Adv.

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“…An elegant cascade process towards challenging oligocyclic systems through the combination of a formal anti ‐carbopalladation with a Suzuki cross‐coupling, was devised by the Werz group [9] . A further cascade process by means of an efficient domino relay metathesis sequences using triallyl 3‐oxindole and indole precursors to access fused bicyclic indoxyl dimers and carbazole derivatives is described in the Communication by the Dash group, [10] while a ligand‐ and additive‐free process developed by the Hoover group allows a straightforward aerobic cobalt‐catalyzed synthesis of 2‐aminobenzimidazoles starting from 2‐aminoanilines [11] . An efficient cobalt‐catalyzed carbonylative ring expansion of oxetanes or thietanes under syngas atmosphere route towards γ‐(thio)butyrolactone is presented by the Dong group [12] .…”

Section: Figurementioning

confidence: 99%

“…[9] A further cascade process by means of an efficient domino relay metathesis sequences using triallyl 3-oxindole and indole precursors to access fused bicyclic indoxyl dimers and carbazole derivatives is described in the Communication by the Dash group, [10] while a ligand-and additive-free process developed by the Hoover group allows a straightforward aerobic cobalt-catalyzed synthesis of 2-aminobenzimidazoles starting from 2-aminoanilines. [11] An efficient cobalt-catalyzed carbonylative ring expansion of oxetanes or thietanes under syngas atmosphere route towards γ-(thio)butyrolactone is presented by the Dong group. [12] The power of ruthenium nanolayers as catalysts for acceptorless dehydrogenative synthesis of quinolones has been demonstrated in the Communication by Chaudhari and Nagaoka.…”

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confidence: 99%

Editorial: The Catalysis of Ring Synthesis

2021

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Ring systems -aromatic or non-aromatic carbocyclic and heterocyclic structures -represent key scaffolds in biologically important molecules. In particular, heterocycles are fundamental building blocks of most small-molecule drugs on the market today. Furthermore, aromatic and heteroaromatic ring systems are of eminent importance for material sciences and are playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes, and photochemical switches, etc.Catalysis, including transition-metal catalysis, organocatalysis, nanocatalysis, photoredox catalysis, has become as a powerful tool for the synthesis of different ring systems. This Special Collection "The Catalysis of Ring Synthesis" covers the most recent strategies of ring synthesis and presents the current advances in the field.A Review by Kotha and co-authors summarizes new synthetic methods to diverse cage polycycles potentially useful for high energy density materials synthesis. [1] In the Review paper by Neto and Zeni the diverse variety of synthesis of pyrrole derivatives using the reaction of alkynes with nitrogencompounds under transition metal-catalyzed and metal-free conditions, is presented. [2] A Minireview from the group of Das reflects the impressive state of the art in photoredox catalysis and the recent applications of photocatalysis to [2 + 2] and [4 + 2] cycloaddition reactions under the irradiation of visible light. [3] Efficient organocatalyzed and/or transition-metal-catalyzed synthesis of azirine, pyridine, piperidine, indole, indoxyl, benzimidazole, carbazole, spiro pyrrolidone, γ-(thio)butyrolactone, quinolone derivatives and oligocyclic systems are reported in a total of 12 Communications. A highly efficient enantioselective organocatalytic synthesis of trisubstituted [a]

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A Facile C‐H Insertion Strategy using Combination of HFIP and Isocyanides: Metal‐Free Access to Azole Derivatives

et al. 2020

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An efficient metal-free approach has been devised towards the synthesis of azoles via CÀ H insertion protocol. Various isocyanides were examined as effective C1-synthons. The HFIP plays crucial role as hydrogen source and promoter of the reaction in order to reveal the maximum efficacies to accomplish the transformation in high yields of the products with excellent functional group tolerance. The control experiment affirmed 83% of deuterium incorporation, when the reaction was performed using HFIP-d 2. Isocyanides are witnessed as significant building blocks in synthetic organic chemistry [1] because of their ability for the reaction with various electrophiles, nucleophiles and radicals. [2] These molecules are also found as benign CO surrogates, ligands in metal complexes and as C1 sources in formal cycloaddition reactions towards the synthesis of valuable targets. [1f-h,2À 3] Furthermore, isocyanides have been extensively explored in engineering a broad spectrum of N-heterocycles. [1a] A large number of useful reports have been noticed on isocyanide insertion owing to their reactivities and efficiencies. In literature, it has been shown that the isocyanides have been utilized as CÀ NÀ C, [4-9] CÀ N [10-12] and C1-source [13-15] to construct various complex molecules (Scheme 1). Further, the reported methodologies are mainly concerned on using the transition metals such as Pd, [4,13,15] Cu, [5,11] Co [6] and Ni. [7,14] In recent years, the isocyanide insertion strategy under non-metal, Lewis-acid, base and photocatalyzed reaction conditions become familiar in the field of organic synthesis. [8,12] It is noteworthy that the isocyanide insertion chemistry under transition metal-free and non-transition metal-free conditions are very rare and remained asserting task for the synthetic chemists. [8-12] In particular, utilizing isocyanides as C1-source has always been explored under transition metal-catalysis. [13-15] In view of this, during our continuous efforts on identifying the transition metal-free catalyzed transformations, [16] we have [a

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Cobalt‐Catalyzed Aerobic Oxidative Cyclization of 2‐Aminoanilines with Isonitriles: Facile Access to 2‐Aminobenzimidazoles

Cited by 5 publications

References 53 publications

Recent achievements in the synthesis of benzimidazole derivatives

Recent achievements in the synthesis of benzimidazole derivatives

Editorial: The Catalysis of Ring Synthesis

A Facile C‐H Insertion Strategy using Combination of HFIP and Isocyanides: Metal‐Free Access to Azole Derivatives

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