Mechanosynthesis of polymeric and binuclear copper complexes <i>via</i> dehydrochlorination and their application in solvent-free C–S bond cross-coupling

Hao, Xiujia; Li, Xinyu; Li, Haitao; Zhang, Xin; Liu, Xiaozhi; Guo, Fang

doi:10.1039/d2ce00624c

Cited by 4 publications

(2 citation statements)

References 35 publications

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“…In 2018, Bolm et al 18 conventional solution-based approaches, Bolm's study provides a more feasible and environmentally friendly route to cobalt(III) catalysts and 2-amidated indoles (Figure 1A). In 2022, Guo et al 19 synthesized copper complexes containing imidazole/benzimidazole ligands by grinding, and successfully applied to C−S coupling, enabling both synthetic and catalytic mechanochemistry. Furthermore, a Liebeskind−Srogl crosscoupling reaction was established for the synthesis of mesosubstituted BODIPYs with high efficiency.…”

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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“…Previously, we mainly focused on the direct solid-state synthesis of coordination complexes by dehydrohalogenation of hydrogen-bonded halometallate salts and then used as the non-noble metal catalyst to implement CÀ S coupling. [26,27] According to the literature, [28] group 10 metals, particularly palladium, and nickel, occupy the forefront positions in chemical reactions. Of these, the unusual properties of nickel have piqued the interest of chemists.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Nickel‐Catalyzed Carbon‐Sulfur Bond Formation between Aryl Iodides and Aromatic Sulfur Surrogates

Hao,

Feng,

Chen

et al. 2023

Chemistry A European J

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The formation of aromatic thioethers from C‐S coupling is of great importance in synthetic chemistry. Traditional solution strategies through transition‐metal catalysis generally require bulk solution, heat, and longer reaction time. Herein, a mechano‐promoted sulfenylation of aryl iodides with nickel catalysis is described. The active aromatic sulfide agents are in‐situ generated from aromatic thiol or disulfide and subsequently adapted in the nickel catalytic cycle, with a tolerance of broad substituted groups under optimized conditions. In addition to the gram‐scale synthesis that reveals the application potential of the method, the radical trap‐ping and competitive experiments are also conducted for the mechanistic study, thus proposing the plausible mechanism rationally. Furthermore, the proposed methodology is certificated as being versatile and following the green principles with ideal calculated values of green chemistry matrix and the comparison with other approaches for C‐S bond formation.

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Mechanochemical tools in the synthesis of organometallic compounds

Aleksanyan

Козлов

2023

Mendeleev Communications

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Mechanosynthesis of polymeric and binuclear copper complexes via dehydrochlorination and their application in solvent-free C–S bond cross-coupling

Cited by 4 publications

References 35 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 Nickel‐Catalyzed Carbon‐Sulfur Bond Formation between Aryl Iodides and Aromatic Sulfur Surrogates

Mechanochemical tools in the synthesis of organometallic compounds

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