Divergent Functionalization of Styrenes via Radical/Polar Crossover with CO₂ and Sodium Sulfinates

Author(s)

Vega, Kimberly Benedetti ; Delgado, Jose Antonio Campos ; Pugnal, Lucas V. B. L. ; Koenig, Burkhard ; Correia, Jose Tiago Menezes ; Paixao, Marcio Weber

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 29, n. 19, p. 9-pg., 2023-02-28.

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 alpha-aryl-acrylates. (AU)

• FAPESP's process: 21/06099-5 - Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications
• Grantee: Márcio Weber Paixão
• Support Opportunities: Regular Research Grants
• FAPESP's process: 21/01354-7 - Photocatalysis applied to difunctionalization of alkenes via CO2 incorporation: multicomponent synthesis of ²-sulfonil and ±- (2-sulfenyl-indolyl) -carboxylic acids
• Grantee: Kimberly Benedetti Vega
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 19/01560-6 - Nickel-catalyzed intermolecular dicarbofunctionalization of unactivated alkenes, employing CO2 and radical precursors
• Grantee: José Tiago Menezes Correia
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• FAPESP's process: 17/10015-6 - Photocatalysis Applied to the Synthesis of N-heterocycles: New Strategies for Intercepting Radical Intermediates Generated in Processes Promoted by Visible-light-Tris (trimethylsilyl)silane Combination.
• Grantee: José Tiago Menezes Correia
• Support Opportunities: Scholarships in Brazil - Post-Doctoral