Divergent Functionalization of Styrenes via Radical/Polar Crossover with CO 2 and Sodium Sulfinates.

Autor: Benedetti Vega K; Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil.; Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany., Campos Delgado JA; Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil.; Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany., Pugnal LVBL; Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil., König B; Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany., Menezes Correia JT; Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil.; Current address: Department of Chemistry, Technical University of Denmark, DK-2800, Kgs. Lyngby, Denmark., Weber Paixão M; Laboratory for Sustainable Organic Synthesis and Catalysis, Department of Chemistry, Federal University of São Carlos - UFSCar, 13565-905, Carlos, São Paulo, Brazil.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Apr 03; Vol. 29 (19), pp. e202203625. Date of Electronic Publication: 2023 Feb 28.
DOI: 10.1002/chem.202203625
Abstrakt: 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 CO 2 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.
(© 2022 Wiley-VCH GmbH.)
Databáze: MEDLINE
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