Multicomponent synthesis of alpha-carboxy-beta-alkylated phosphonates mediated by visible light using CO2 and RBF3K

• Grant number: 23/08283-3
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: September 01, 2023
• Status: Discontinued
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: André Luiz Carvalho de Oliveira
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated scholarship(s): 25/03853-1 - Multicomponent synthesis of alpha-carboxy-beta-alkylated phosphonates mediated by visible light using [13C, 14C] CO2, BE.EP.IC

Abstract

The photocatalytic insertion of a molecule of CO2 in organic structures is considered to be an advantageous strategy to achieve carboxylic acids and it's derivatives with a concomitant extension of the carbonic chain. Such methodologies generate high value-added products in a sustainable manner. Currently, photocatalytic protocols promoting the incorporation of CO2 in organic molecules have already been described, however, vinyl phosphonates - high synthetic potential olefinic construction blocks - have not been yet explored as reaction partners in systems involving the use of CO2. Therefore, there is still room for the development of broader studies, mechanistical and in the need of enlarging the known chemical space.Recently, the fusion between organotrifluoroborates and photocatalysis have led to the development of new methodologies with high atomic economy, for the construction of highly complex chemical scaffolds, which wouldn't be easily accessible in a single step, using available radical precursors.In this context, the present research project proposes the investigation of multicomponent photocatalytic reactions via a radical-polar crossover mechanism to the achievement of alpha-carboxy-beta-alkylated phosphonates, from vinyl phosphonates, organotrifluoroborates as radical precursors and CO2 as the carboxylation agent, in the presence of visible light.

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; 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)