Multicomponent synthesis of alpha-carboxy-beta-alkylated phosphonates mediated by visible light using [13C, 14C] CO2

• Grant number: 25/03853-1
• Support Opportunities: Scholarships abroad - Research Internship - Scientific Initiation
• Start date: May 01, 2025
• End date: July 31, 2025
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: André Luiz Carvalho de Oliveira
• Supervisor: Burkhard Koenig
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Institution abroad: University of Regensburg, Germany
• Associated to the scholarship: 23/08283-3 - Multicomponent synthesis of alpha-carboxy-beta-alkylated phosphonates mediated by visible light using CO2 and RBF3K, BP.IC

Abstract

The synthesis of isotopically marked molecules with carbon-14 labels usually presents a challenge since 14C atoms ultimately comes from 14CO2. Classically the incorporation of CO2 into organic molecules relies on the use of highly reactive nucleophiles (such as organolithium and Grignard reagents) and harsh reaction conditions, requiring early installation of this moiety, and so limiting synthetic possibilities.This project proposes to apply a photocatalytic methodology, overcoming this challenge, for the synthesis of ¿-phosphonate carboxylic acids of potential interest, through the difunctionalization of the double bond of a vinylic phosphonate, with direct incorporation of 13/14CO2 and concomitant extension of the alkyl chain via a carbon-centered radical insertion.