Copper-Catalyzed Carboxylation of Aryl Thianthrenium Salts with CO2

Shibiao Tang; Xiaobo Zhao; Lidong Yang; Bin Li; Baiquan Wang

doi:10.1002/anie.202212975

Copper-Catalyzed Carboxylation of Aryl Thianthrenium Salts with CO₂

Angew Chem Int Ed Engl. 2022 Nov 21;61(47):e202212975. doi: 10.1002/anie.202212975. Epub 2022 Oct 21.

Authors

Shibiao Tang¹, Xiaobo Zhao¹, Lidong Yang¹, Bin Li¹, Baiquan Wang^{1

2}

Affiliations

¹ State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 30007, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

PMID: 36195552
DOI: 10.1002/anie.202212975

Abstract

Carboxyl group is one of the most widely used groups in organic synthesis. Herein, an efficient copper-catalyzed carboxylation of aryl thianthrenium salts with carbon dioxide (CO₂ ) at room temperature has been developed. The reaction employs low loading of cuprous chloride catalyst under 1 atm 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.

Keywords: Carbon Dioxide; Carboxylation; Copper; C−H Functionalization; Sulfonium Salts.

Abstract

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