Photocatalysis applied to difunctionalization of alkenes via CO2 incorporation: multicomponent synthesis of ²-sulfonil and ±- (2-sulfenyl-indolyl) -carboxylic acids

• Grant number: 21/01354-7
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: July 01, 2021
• End date: August 31, 2025
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Kimberly Benedetti Vega
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated research grant: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock, AP.PCPE
• Associated scholarship(s): 23/05334-6 - Chasing sustainability: photoinduced synthesis of dicarboxylic systems from alkenes via CO2 or a CO2/carbamoyl-radical cocktail, BE.EP.DR

Abstract

The compounds containing different functional groups are of considerable importance in the theoretical understanding of the transformations that lead to their synthesis and in the application of new molecules in synthetic organic chemistry. Interestingly, the chemical properties of each functional group can be changed through steric and electronic modifications, combined with the effects of the adjacent functional groups. Therefore, new chemical properties can be expected for such compounds, which can lead to the development of molecules with a wide application in the pharmaceutical, materials or fine chemistry fields. One of the approaches of chemistry that reaches the synthesis of densely functionalized compounds is the visible light photoredox catalysis, which, unlike classical approaches, offers access to transformations of target molecules efficiently, under milder conditions that are in line with the precepts of green chemistry. In this sense, this project aims to develop two protocols aimed at forming C - S and C - C bonds, addressing the photochemical concepts related to photocatalytic carbosulfonylation/sulfenylation of electron-rich species using CO2 and R-SO2Na/RSH. These protocols will provide the obtaining of several compounds with biological potential, which will be evaluated against the new Coronavirus (SARS-CoV-2). (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

VEGA, KIMBERLY BENEDETTI; DELGADO, JOSE ANTONIO CAMPOS; PUGNAL, LUCAS V. B. L.; KOENIG, BURKHARD; CORREIA, JOSE TIAGO MENEZES; PAIXAO, MARCIO WEBER. Divergent Functionalization of Styrenes via Radical/Polar Crossover with CO₂ and Sodium Sulfinates. CHEMISTRY-A EUROPEAN JOURNAL, v. 29, n. 19, p. 9-pg., 2023-02-28. (21/06099-5, 21/01354-7, 19/01560-6, 17/10015-6)

VEGA, KIMBERLY BENEDETTI; DE OLIVEIRA, ANDRE LUIZ CARVALHO; KONIG, BURKHARD; PAIXAO, MARCIO WEBER. Visible-Light-Induced Synthesis of 1,2-Dicarboxyl Compounds from Carbon Dioxide, Carbamoyl-dihydropyridine, and Styrene. ORGANIC LETTERS, v. 26, n. 4, p. 6-pg., 2024-01-22. (23/08283-3, 23/05334-6, 21/06099-5, 21/01354-7)

PUGNAL, LUCAS V. B. L.; VEGA, KIMBERLY B.; PISSINATI, EMANUELE F.; CORREIA, JOSE TIAGO M.; ZUKERMAN-SCHPECTOR, JULIO; MARTIN, RUBEN; PAIXAO, MARCIO W.. 1,2-Arylsulfonylation of Vinyl Ethers and Esters Enabled by Dual Ni Catalysis. CHEMCATCHEM, v. N/A, p. 6-pg., 2023-06-19. (21/06099-5, 19/01560-6, 20/09353-7, 22/04597-0, 17/10015-6, 21/01354-7)