Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate

Kederienė, Vilija; Jaglinskaitė, Indrė; Voznikaitė, Paulina; Rousseau, Jean-Paul; Rollin, Patrick; Šačkus, Algirdas; Tatibouët, Arnaud

doi:10.3390/molecules26226822

Cited by 2 publications

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References 67 publications

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“…Molecule CuI:Ligand (Ratio) [b] Ligand (L) Product, Yield (%) Copper-catalyzed coupling reactions was performed by applying standard conditions with various copper ligands and copper iodide, which was chosen for its air stability [51][52][53]. We first chose the D-arabino derivative 5 with 4-iodoanisole as a model substrate to optimize the catalytic S-arylation (Scheme 4, Table 1).…”

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confidence: 99%

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Kederienė

Rousseau²,

Schuler

et al. 2022

Molecules

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The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a copper-catalyzed C-S bond formation with aryl iodides. Chemoselective S-arylation was observed, with copper iodide and dimethylethylenediamine (DMEDA) as the best ligand in dioxane at 60–90 °C. The corresponding chiral oxazolines were obtained in reasonable to good yields under relatively mild reaction conditions. This approach is cheap, as using one of the cheapest transition metals, a simple protocol and various functional group tolerance make it a valuable strategy for getting S-substituted furanose-fused OZT. The structures of the novel carbohydrates were confirmed by NMR spectroscopy and an HRMS analysis.

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Section: Entrymentioning

confidence: 99%

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Kederienė

Rousseau²,

Schuler

et al. 2022

Molecules

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Transition Metal Complexes with Amino Acids, Peptides and Carbohydrates in Catalytic Asymmetric Synthesis: A Short Review

Titova

2024

Processes

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The present review is devoted to the application of transition metal complexes with such ligands as amino acids, peptides and carbohydrates in catalysis. The literature published over the past 20 years is surveyed. Among the distinctive features of these ligands are their versatility, optical activity, stability and availability. Furthermore, depending on the specific synthetic task to be solved, these ligands open up almost infinite opportunity for modification. Largely thanks to their multifaceted reactivity, transition metal complexes with amino acids, peptides and carbohydrates can catalyze most of the known chemical reactions affording optically pure compounds. In this review, the emphasis is placed upon C(sp3)–H activation, cross-coupling and hydrogenation (including traditional hydrogenation in the presence of hydrogen gas and hydrogenation with hydrogen transfer) reactions. The choice is not accidental, since these reactions on the one hand display the catalytic versatility of the above complexes, and on the other hand, they are widely employed in industry.

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Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate

Cited by 2 publications

References 67 publications

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Transition Metal Complexes with Amino Acids, Peptides and Carbohydrates in Catalytic Asymmetric Synthesis: A Short Review

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