Visible-Light-Induced Synthesis of 1,2-Dicarboxyl Compounds from Carbon Dioxide, Carbamoyl-dihydropyridine, and Styrene

Author(s)

Vega, Kimberly Benedetti ; de Oliveira, Andre Luiz Carvalho ; Konig, Burkhard ; Paixao, Marcio Weber

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 26, n. 4, p. 6-pg., 2024-01-22.

Abstract

beta-Amidated carboxylic acids, or succinamic acid derivatives, constitute a valuable chemical scaffold with broad applications in pharmaceuticals, agrochemicals, and polymer sciences. Herein, we report a redox-neutral multicomponent reaction for the synthesis of succinamic acid derivatives in good yields. This protocol involves styrene, CO(2 )and 1,4-carbamoyl-dihydropyridine as radical precursors. The method exhibits a broad substrate scope under mild reaction conditions, including late-stage functionalization. Moreover, by employing (CO2)-C-13, the method enables the synthesis of labeled 1,2-dicarboxylic compounds. (AU)

• FAPESP's process: 23/08283-3 - Multicomponent synthesis of alpha-carboxy-beta-alkylated phosphonates mediated by visible light using CO2 and RBF3K
• Grantee: André Luiz Carvalho de Oliveira
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• FAPESP's process: 23/05334-6 - Chasing sustainability: photoinduced synthesis of dicarboxylic systems from alkenes via CO2 or a CO2/carbamoyl-radical cocktail
• Grantee: Kimberly Benedetti Vega
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• 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