Copper(II)-Mediated, Site-Selective C(sp<sup>2</sup>)–H Sulfonamidation of 1-Naphthylamines

Hajra, Arun Kumar; Ghosh, Prasanjit; Paul, Priyanka; Kundu, Mrinalkanti; Das, Sajal

doi:10.1021/acs.joc.3c01852

Cited by 5 publications

(1 citation statement)

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“…Ligand directed Cu(II)-catalyzed sulfonamidation was accomplished by Yu group, who reported a Cu(II)-catalyzed oxazolyamide directing group-mediated sulfonamidation of arenes and heteroarenes using aryl/alkyl sulfonamides to obtain the corresponding ortho -sulfonamide derivatives . Subsequently, many research groups have reported Cu(II)-catalyzed directed C–H sulfonamidation reactions . However, the development of a new general method for forming these important functionalities through C–H-activated C–X bond formation is crucial for the advancement of this field.…”

Section: Introductionmentioning

confidence: 99%

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

Pati,

Molla,

Ghosh

et al. 2024

J. Org. Chem.

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We have demonstrated N-substituted 2-pyridones as an N,Odirecting group for selective C(sp 2 )-H-activated thiolation, selenylation, and sulfonamidation of ortho C−H bonds of benzamides. This method utilizes a costeffective Cu(II)-salt catalyst instead of precious metal catalysts, achieving high yields, including gram-scale synthesis and excellent functional group tolerance. We applied this protocol to access 30 different compounds with high yields, demonstrating thiolation of fluorine-substituted benzamides as well. Density functional theory (DFT) calculations support the mechanism, including acetatesupported concerted metalation deprotonation (CMD) steps and the unique role of dimethyl sulfoxide (DMSO) solvent. The facile synthesis of pharmaceutically important sulfonamides and other compounds highlights the method's potential in chemistry and medicinal chemistry.

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Section: Introductionmentioning

confidence: 99%

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

Pati,

Molla,

Ghosh

et al. 2024

J. Org. Chem.

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Recent advances in site-selective C H functionalization of naphthalenes: An update 2020–2024

Li,

Chen,

Dong

et al. 2025

Tetrahedron Letters

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Palladium-Catalyzed, Site-Selective C(sp²)8–H Halogenation and Nitration of 4-Quinolone Derivatives

Das,

Ghosh,

Ghosh

et al. 2024

J. Org. Chem.

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Selective installation of halo and nitro groups in heterocyclic backbone through a transition-metal-catalyzed C−H bond activation strategy is immensely alluring to access high-value scaffolds. Here in, we disclosed N-pyrimidyl-directed assisted palladium(II)-catalyzed C(sp 2 )8−H halogenation and nitration of substituted 4-quinolone derivatives in the presence of Nhalosuccinimide and tert-butyl nitrite, respectively, offering structurally diversified 8-halo/nitro-embedded 4-quinolone frameworks in high yields. Mechanistic studies indicated that the reaction follows an organometallic pathway with a reversible C−H metalation step. This operationally simple protocol is scalable with a broad substrate scope and excellent functional group compatibility. Moreover, the postdiversifications of the synthesized derivatives are also showcased to ensure the synthetic versatility of the methodology.

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Copper(II)-Mediated, Site-Selective C(sp²)–H Sulfonamidation of 1-Naphthylamines

Cited by 5 publications

References 56 publications

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

Recent advances in site-selective C H functionalization of naphthalenes: An update 2020–2024

Palladium-Catalyzed, Site-Selective C(sp²)8–H Halogenation and Nitration of 4-Quinolone Derivatives

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Copper(II)-Mediated, Site-Selective C(sp2)–H Sulfonamidation of 1-Naphthylamines

Cited by 5 publications

References 56 publications

2-Pyridone-Directed CuII–Catalyzed General Method of C(sp2)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

2-Pyridone-Directed CuII–Catalyzed General Method of C(sp2)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

Recent advances in site-selective C H functionalization of naphthalenes: An update 2020–2024

Palladium-Catalyzed, Site-Selective C(sp2)8–H Halogenation and Nitration of 4-Quinolone Derivatives

Contact Info

Product

Resources

About

Copper(II)-Mediated, Site-Selective C(sp²)–H Sulfonamidation of 1-Naphthylamines

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

2-Pyridone-Directed Cu^II–Catalyzed General Method of C(sp²)-H Activation for C–S, C–Se, and C–N Cross-Coupling: Easy Access to Aryl Thioethers, Selenide Ethers, and Sulfonamides and DFT Study

Palladium-Catalyzed, Site-Selective C(sp²)8–H Halogenation and Nitration of 4-Quinolone Derivatives