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【Baiquan Wang】Copper-Catalyzed Carboxylation of Aryl Thianthrenium Salts with CO2

Source:WileyChem   Date:2022/11/30

As one of the major greenhouse gases, carbon dioxide (CO2) plays a crucial role in global warming and climate change. In another aspect, CO2 could serve as a green, nontoxic, abundant, and renewable C1 building block for organic synthesis. Thus, the chemical fixation and utilization of carbon dioxide gained increasing interest, especially to construct valuable carboxylic acids, which are pivotal building blocks in the various natural products and pharmaceuticals. In recent years, direct carboxylation reactions of halogenated aromatics and their analogues with CO2 have been reported successively, but direct carboxylation reactions of complex molecular skeletons with CO2 are still unachievable.


Recently, Baiquan Wang’ group achieved an efficient copper-catalyzed carboxylation of aryl thianthrenium salts with CO2 at room temperature. The reaction employs low loading of cuprous chloride catalyst under 1atm CO2 and exhibits good functional group tolerance. In combination with C−H thianthrenation of aromatic hydrocarbons, this work provides an efficient method for the site-selective C−H carboxylation of aromatic hydrocarbons. It may serve as a significant late-stage carboxylation tool for the modification of drug molecules in the future. Relevant achievements were published in Angew. Chem. Int. Ed., 2022, DOI: 10.1002/anie.202212975.