Bis(2-pyridyl)diselenoethers as versatile ligands for copper-catalyzed C–S bond formation in glycerol

Cargnelutti, Roberta; Lang, Ernesto S.; Schumacher, Ricardo F.

doi:10.1016/j.tetlet.2015.07.060

Cited by 26 publications

(5 citation statements)

References 47 publications

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“…344 Bis(2-pyridyl)diselenoethers with different bridges can serve as ligands in the Ullmann cross-coupling, and the best results were obtained with the diselen ligand with four methylene units. 345 A large series (15 compounds) were synthesized via the reaction of aryl/heteroaryl iodides, including di-ortho- However, many reactions can be carried out without a ligand. This fact is especially important since copper, due to its relatively low cost and low toxicity of its salts and oxides, has become the most popular catalyst in cross-coupling reactions; therefore, such catalysts can be in demand in industry.…”

Section: Catalytic Cross-coupling Reactions (mentioning

confidence: 99%

“…Bis(2-pyridyl)diselenoethers with different bridges can serve as ligands in the Ullmann cross-coupling, and the best results were obtained with the diselen ligand with four methylene units . A large series (15 compounds) were synthesized via the reaction of aryl/heteroaryl iodides, including di- ortho -substituted iodides, which produced high yields (78–99%) with thiols, while with alkyl thiols, the yields decreased.…”

Section: Catalytic Cross-coupling Reactions (Z = S Se Te)mentioning

confidence: 99%

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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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Section: Catalytic Cross-coupling Reactions (mentioning

confidence: 99%

Section: Catalytic Cross-coupling Reactions (Z = S Se Te)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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“…More recently, Cargnelutti et al described a straightforward C-S coupling of aryl halides (18) with thiols (19) in glycerol, catalyzed by CuI/bis(2-pyridyl)diselenoethers and using ultrasound (as alternative energy source) to accelerate the process (Scheme 7) [28]. The efficiency of such C-S couplings in glycerol is analogous to other cross-coupling reactions in toxic organic solvents, which also employ more expensive catalysts based on transition metals.…”

Section: Catalyst (10 Mol %)mentioning

confidence: 99%

Merging Metallic Catalysts and Sonication: A Periodic Table Overview

et al. 2017

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Abstract:This account summarizes and discusses recent examples in which the combination of ultrasonic waves and metal-based reagents, including metal nanoparticles, has proven to be a useful choice in synthetic planning. Not only does sonication often enhance the activity of the metal catalyst/reagent, but it also greatly enhances the synthetic transformation that can be conducted under milder conditions relative to conventional protocols. For the sake of clarity, we have adopted a structure according to the periodic-table elements or families, distinguishing between bulk metal reagents and nanoparticles, as well as the supported variations, thus illustrating the characteristics of the method under consideration in target synthesis. The coverage focuses essentially on the last decade, although the discussion also strikes a comparative balance between the more recent advancements and past literature.

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“…Thioetherification of aryl iodides and activated aryl bromides with aromatic or aliphatic thiols was developed in the presence of CuI as the catalyst and diselenoethers as the ligands (Scheme 39). 42 No reaction was observed in the absence of the catalyst. However, moderate yield was obtained in the absence of the ligand.…”

Section: Reactions Involving C-x (X=halogen) Bond Cleavagementioning

confidence: 99%

Advances in transition-metal catalyzed thioetherification reactions of aromatic compounds

Ghaderi

2016

Tetrahedron

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Bis(2-pyridyl)diselenoethers as versatile ligands for copper-catalyzed C–S bond formation in glycerol

Cited by 26 publications

References 47 publications

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

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

Merging Metallic Catalysts and Sonication: A Periodic Table Overview

Advances in transition-metal catalyzed thioetherification reactions of aromatic compounds

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