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Copper(I) Iodide Catalyzed [3+3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds

ORGANIC LETTERS (2023)

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Indolizine Synthesis through Annulation of Pyridinium 1,4-Thiolates and Copper Carbenes: A Predictive Catalysis Approach

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Summary: Predictive catalysis was used to study the reaction between pyridinium 1,4-zwitterionic thiolates and a copper carbene. Theoretical calculations were performed to assess the suitability of their annulation reaction and predict the performance of different copper salts, diazo species, and pyridinium derivatives. The experimental conditions were optimized based on these calculations, the scope of the reaction was evaluated, and the accuracy of the predictions was assessed. Indolizine scaffolds were synthesized with yields up to 90% in the reactivity of pyridinium 1,4-zwitterionic thiolates with a metal carbene.

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Summary: A difluorocarbene-triggered [1+5] annulation reaction was developed to directly access 1,1-difluoro-1,9a-dihydropyrido[2,1-c][1,4]-thiazine-3,4-dicarboxylate derivatives in satisfactory to good yields by reacting potassium bromodifluoroacetate and pyridinium 1,4-zwitterionic thiolates under heating. The pyridinium 1,4-zwitterionic thiolates first attack the difluorocarbene generated from potassium bromodifluoroacetate, followed by an intramolecular nucleophilic addition to the pyridiniums. This method provides a rapid route for introducing the difluoromethyl group into the 1,9a-dihydropyrido[2,1-c][1,4]thiazine ring, and even for modifying drug molecules.

ORGANIC LETTERS (2023)

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Rh(iii)-catalyzed C-H/C-C bond annulation of enaminones with iodonium ylides to form isocoumarins

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