A nickel-catalyzed carbon–sulfur cross-coupling reaction with disulfides enabled by mechanochemistry

Hao, Xiujia; Feng, Daming; Huang, Peng; Guo, Fang

doi:10.1039/d4qo00069b

Cited by 5 publications

(1 citation statement)

References 49 publications

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“…In addition, reduced Schiff base ligands exhibit greater flexibility than pristine ones, affording them increased coordination versatility. Given that zinc complexes are heterogeneous, nontoxic, noncorrosive, cost-effective, stable, and environmentally benign catalysts, − as well as our continuing interest in mechanochemistry, − the Zn(II) complexes bearing reduced Schiff base ligands, N , N′ - diphenylethylenediamine (L 1 ) , were initially synthesized by grinding. Subsequently, an appropriate amount of the reactant substrate was employed in a mechanochemical C–S bond cross-coupling within the same vessel, thereby achieving a continuous mechanochemical process from synthesis to catalysis in a one-pot, two-step approach and avoiding the catalyst purification procedures (Figure B).…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Cascade Synthesis of Zinc Complexes for Catalytic C–S Coupling in One-Pot

Feng,

Hao,

Fei

et al. 2024

Organometallics

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The mechanochemical approach to transition metal catalysis offers a number of advantages, including a reduction in solvent usage and an acceleration of reaction times. This study elucidates a one-pot, two-step cascade catalytic synthesis enabled by mechanochemistry, which integrates the synthesis of bidentate zinc complexes and their application in carbon−sulfur coupling reactions. The zinc complexes were systematically modified by altering the halogen atoms attached to the metal center, utilizing the reduced Schiff base ligand N,N'-diphenylethylenediamine, which significantly influenced the catalytic efficiency. Under optimal conditions, a wide range of thioether products were synthesized, demonstrating broad applicability across various substrates. The mechanistic insights were enhanced through the execution of free radical trapping experiments and analysis of reaction intermediates, revealing an S N 2 substitution mechanism in the formation of carbon−sulfur bond. Furthermore, the methodology adheres to green chemistry principles, as evidenced by the favorable green chemistry metrics obtained, indicating a sustainable and eco-friendly protocol for practical use.

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Section: Introductionmentioning

confidence: 99%

Mechanochemical Cascade Synthesis of Zinc Complexes for Catalytic C–S Coupling in One-Pot

Feng,

Hao,

Fei

et al. 2024

Organometallics

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Mechanochemical synthesis and catalysis of dinuclear Cu (II) complexes in C–S coupling

Guo,

Fei,

Hao

et al. 2024

Applied Organom Chemis

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This study introduces a mechanochemical approach for synthesizing dinuclear Cu (II) complexes and applying them directly in C–S coupling reactions, offering a sustainable alternative to traditional solvent‐based syntheses. The mechanochemical method, recognized for its environmental advantages and efficiency, was employed to synthesize the Cu (II) complex [CuL(μ‐Cl)Cl2] (I) and the metal–organic salt 2L.2[CuCl4]2− (II), thereby minimizing solvent use and waste production. The synthesized complex I exhibited superior catalytic activity in C–S coupling, achieving a 96% yield within 20 min with methanol serving as a grinding medium. The mechanochemical process was further refined and confirmed for its environmental sustainability, with an E‐factor of 0.460 and an EcoScale score of 78. This synthetic method not only shortens reaction times and reduces solvent use but also streamlines the operational procedure, providing a more environmentally benign and economically viable route for C–S coupling. The research highlights the potential of mechanochemistry in simplifying synthetic processes and enhancing their sustainability, paving the way for future advancements in green synthetic strategies.

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Mechano-driven chemical reactions

Li,

Liu,

Wang

et al. 2024

Green Energy & Environment

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A nickel-catalyzed carbon–sulfur cross-coupling reaction with disulfides enabled by mechanochemistry

Abstract: Herein, a facile and efficient thiolation method is presented, involving Ni-catalyzed cross-coupling of readily available disulfides with diverse bromides, promoted by ball milling. This Ni-catalyzed modular approach demonstrates excellent functional...

Cited by 5 publications

References 49 publications

Mechanochemical Cascade Synthesis of Zinc Complexes for Catalytic C–S Coupling in One-Pot

Mechanochemical Cascade Synthesis of Zinc Complexes for Catalytic C–S Coupling in One-Pot

Mechanochemical synthesis and catalysis of dinuclear Cu (II) complexes in C–S coupling

Mechano-driven chemical reactions

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