Nickel-Catalyzed Coupling of Aryl O-Carbamates With Grignard Reagents: 2,7-Dimethylnaphthalene

Dallaire, Carol; Kolber, Isabelle; Gingras, Marc; Kitamura, M.; Narasaka, Koichi

doi:10.15227/orgsyn.078.0042

Cited by 22 publications

(2 citation statements)

References 12 publications

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“…Most of these compounds are sensitive to moisture, colorless, and soluble in nonpolar organic solvents 13 . Due to the influence of amino groups, these substances are less sensitive to the hydrolytic than ordinary acid chlorides 14 . The reactions of carbamoyl chloride with an alcohol or phenol led to stable carbamate esters (urethanes) 11 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 3-Dimethyl Carbamoyl Emodin

Firdayani,

Listiana,

Witanto

2023

Valensi

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Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a natural anthraquinone derivative with potential pharmacological such as cytotoxic effects. The structure modification could be performed to determine the functional groups that have the role of substance activities. In this study, we modified one hydroxy group in the emodin structure to become dimethyl carbamoyl moiety. Emodin was reacted with dimethyl carbamoyl chloride and potassium carbonate to create 3-dimethyl carbamoyl emodin. The structure of the product was elucidated using mass spectrophotometer (MS), Fourier transform infrared (FTIR), proton and carbon nuclear magnetic resonance (H-NMR and C-NMR). These substances were tested for cytotoxicity against HepG2 cell lines using the MTT assay. According to the evaluation, 3-dimethyl carbamoyl emodin is less cytotoxic than emodin. As a result, the hydroxy group at the C3 position of emodin has been identified as a functional component that contributes to its cytotoxic effect.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 3-Dimethyl Carbamoyl Emodin

Firdayani,

Listiana,

Witanto

2023

Valensi

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“…Its retrosynthetic analysis is depicted in Scheme . In the penultimate step, the selective removal of the incipient 9-OH of the phenanthrol is carried out by transfer hydrogenation of the corresponding triflate or β-hydride-induced excision of the corresponding O-carbamate under Ni-catalyzed conditions, a procedure of considerable, as yet unfulfilled, promise. , In this work, we also advantageously adapted the silicon protection tactic for most reactive DoM sites , (A, Scheme ) and the regioselective ipso-halodesilylation. Finally, we report on an apparent kinetic, thermodynamic ortho, remote metalation selectivity (B, Scheme ) that allows the additional regioselective electrophile introduction into biaryl systems and thence leads to more highly substituted phenanthrenes.…”

Section: Introductionmentioning

confidence: 99%

Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

et al. 2015

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A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling-directed remote metalation (DreM) sequence is reported. Diversity to this methodology was achieved by a regioselective DoM rather than DreM reaction, affording more highly substituted phenanthrols ( Table 2 ). Application of the turbo-Grignard reagent (i-PrMgCl·LiCl) in the Ni-catalyzed Corriu-Kumada reaction gave efficient decarbamoylation ( Tables 3 and 4 ). Additional features are the TMS protecting group and halo-induced ipso-desilylation tactics applied to the regioselective synthesis of phenanthrenes ( Scheme 2 ).

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The Directed ortho‐Metallation (DoM) Cross‐Coupling Nexus. Synthetic Methodology for the Formation of Aryl‐Aryl and Aryl‐Heteroatom‐Aryl Bonds

Anctil¹,

Snieckus²

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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Nickel-Catalyzed Coupling of Aryl O-Carbamates With Grignard Reagents: 2,7-Dimethylnaphthalene

Cited by 22 publications

References 12 publications

Synthesis and Cytotoxic Evaluation of 3-Dimethyl Carbamoyl Emodin

Synthesis and Cytotoxic Evaluation of 3-Dimethyl Carbamoyl Emodin

Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

The Directed ortho‐Metallation (DoM) Cross‐Coupling Nexus. Synthetic Methodology for the Formation of Aryl‐Aryl and Aryl‐Heteroatom‐Aryl Bonds

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