Electrosynthesis of Heterocyclic Compounds and Selective Fluorination by Electrochemical Cyclization with Sacrificial Electrodes

• Grant number: 23/04144-9
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: June 01, 2023
• End date: May 31, 2024
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Guilherme Batista Simoso
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

In this undergraduate project, we aim to develop a new synthetic route for isochromane and isochromene derivatives through cyclization reactions in electrosynthesis using sacrificial electrodes (Figure 1). From this approach, the project was conceived in two phases: Initially, from the derivatives of 2-alkynil-benzaldehydes (1) and 2-alkenil-benzaldehydes (2) we propose the synthesis of derivatives of isochromenes (3) and isochromans ( 4), respectively. In the second phase of this project, we propose the synthesis of fluorinated and trifluoromethylated derivatives (isochromenes (5) and isochromans (6)). The sacrificial electrodes proposed for these transformations are: Silver (Ag), copper (Cu), zinc (Zn), magnesium (Mg) and aluminum (Al). We also propose the variation of alcohols, as well as the substituents on the benzene ring.We emphasize that fluorination reactions are extremely important in the synthesis of compounds with potential biological activities, mainly in the pharmaceutical industry, due to the unique properties of fluorinated compounds. Fluorinated molecules can provide a significant increase in thermodynamic stability, lipophilicity and affinity for target proteins of organic compounds.This project will also have the co-supervision of Dr. Guilherme Martins, who works as a postdoc for our team and is a FAPESP fellow proc. 2022/00074-3.