A Chemoselective and Desulfurative Chan–Lam Coupling: C–N Bond Formation between Benzimidazoline‐2‐Thiones and Arylboronic Acids

Chen, Jinquan; Liu, Xing; Guo, Jia; Dong, Zhi‐Bing

doi:10.1002/ejoc.202000075

Cited by 13 publications

(6 citation statements)

References 84 publications

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“…Then, TS-A in the presence of boron species ( 10 or 11 ) forms a transition state intermediate TS-B (C–N bond formation). Upon reductive elimination, TS-B converts into an aryl nitrilium ion TS-C , releasing the copper catalyst back to the catalytic cycle via oxidation by O 2 (air) . At the same time, deprotonation of the acidic proton of the ortho -acetyl group ( TS-D ) followed by subsequent addition onto the nitrilium carbon results in ring-closing C–C bond formation, producing the intermediate TS-E .…”

Section: Mechanismmentioning

confidence: 99%

Cu-Catalyzed Tandem C–N and C–C Bond Formation Leading to 4(1H)-Quinolones: A Scaffold with Diverse Biological Properties from Totally New Raw Materials in a Single Step

Tummanapalli,

Gulipalli,

Bodige

et al. 2024

J. Org. Chem.

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A novel Cu-catalyzed tandem C−N and C−C bondformation reaction has been developed to furnish 2-substituted-4-(1H)-quinolones. 4-(1H)-quinolones play an important role in medicinal chemistry. Many 2-aryl(alkyl)-4(1H)-quinolones are found to exhibit diverse biological properties. While traditional methods have inherent issues [like starting materials with incompatible functional groups (NH 2 and keto groups)], many modern methods either require activated starting materials (like Ynones) or employ expensive metals (Pd, Rh, Au, etc.) involving carbonylation using CO or metal complexes. Our protocol presents an environmentally friendly one-step method for the construction of these useful 2-substituted-4-(1H)-quinolones from easily available aryl boronic acid (or pinacolate ester) and nitriles as new raw materials, using a cheap Cu-catalyst and O 2 (air) as a green oxidant. We further extended its application to the synthesis of various natural products, including the first formal total synthesis of punarnavine. A plausible mechanism involving an aryl nitrilium ion (formed due to the intermolecular C−N bondforming coupling between aryl boron species and the nitrile group) followed by tandem intramolecular C−C bond formation has been proposed.

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Section: Mechanismmentioning

confidence: 99%

Cu-Catalyzed Tandem C–N and C–C Bond Formation Leading to 4(1H)-Quinolones: A Scaffold with Diverse Biological Properties from Totally New Raw Materials in a Single Step

Tummanapalli,

Gulipalli,

Bodige

et al. 2024

J. Org. Chem.

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“…Moreover, under alkaline conditions and at higher temperatures, desulfurization with the formation of N-arylbenzimidazole occurred (Scheme 146, C). 563 thioxoimidazolidin-4-ones produced S-aryl-substituted 2-thiohydantoins under mild conditions. The compounds had a certain anticancer activity (Scheme 146, D (1)).…”

Section: Catalytic Cross-coupling Reactions (mentioning

confidence: 99%

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

2022

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In the present review, we discuss recent progress in the field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are consideredcatalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

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“…Later developments have significantly contributed to overcoming these drawbacks, making Chan-Lam cross-coupling a preferred C-N bond-forming approach over existing protocols. [35][36][37][38][39][40][41][42] Chan-Lam cross-couplings are also strategies of choice for the formation of target bonds in multi-step reactions; designed for the synthesis of significant heterocyclic scaffolds. Some of these reactions are assisted by visible light as well.…”

Section: Introductionmentioning

confidence: 99%

N,N′-Dimethylurea as an efficient ligand for the synthesis of pharma-relevant motifs through Chan–Lam cross-coupling strategy

et al. 2023

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A Chemoselective and Desulfurative Chan–Lam Coupling: C–N Bond Formation between Benzimidazoline‐2‐Thiones and Arylboronic Acids

Cited by 13 publications

References 84 publications

Cu-Catalyzed Tandem C–N and C–C Bond Formation Leading to 4(1H)-Quinolones: A Scaffold with Diverse Biological Properties from Totally New Raw Materials in a Single Step

Cu-Catalyzed Tandem C–N and C–C Bond Formation Leading to 4(1H)-Quinolones: A Scaffold with Diverse Biological Properties from Totally New Raw Materials in a Single Step

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

N,N′-Dimethylurea as an efficient ligand for the synthesis of pharma-relevant motifs through Chan–Lam cross-coupling strategy

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