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Published on: November 9, 2019
Divergent Functionalization of Styrenes via Radical/Polar Crossover with CO2 and Sodium Sulfinates
Kimberly Benedetti Vega1,2, José Antonio Campos Delgado1,2, Lucas V B L Pugnal1
1Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil.
Abstract:
Sulfones and carboxylic acids are prominent motifs widely present in the chemical structure of agrochemicals, pharmaceuticals and many other highly valuable compounds. Herein, we describe a conjunctive strategy for the precise installation of these functionalities onto styrenes using sodium sulfinates and CO2 as coupling partners. The protocol allowed the preparation of carboxy-sulfonylated compounds in good yields and broad functional group tolerance. Additionally, taking advantage of the leaving group ability of the sulfone moiety, a one-pot photocatalytic carboxy-sulfonylation-elimination strategy was developed for the synthesis of α-aryl-acrylates.
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