Visible-light photoredox C-H functionalization of heteroarenes with aminonitriles

• Grant number: 19/10608-2
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate (Direct)
• Start date: October 07, 2019
• End date: March 18, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Arlene Gonçalves Corrêa
• Grantee: Natália Menezes Moreira Borges
• Supervisor: Till Opatz
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Institution abroad: Johannes Gutenberg University Mainz (JGU), Germany
• Associated to the scholarship: 17/19940-4 - Synthesis and evaluation of antiparasitic activity of quinazolines employing multicomponent reactions and C-H functionalization, BP.DD

Abstract

Aminonitriles are important intermediates in organic synthesis, since this structure can be used as a building block on the synthesis of several heterocyclic compounds. The versatile reactivity of these structures is due to the presence of an acidic hydrogen in the ±-position of amino and cyano groups. The most common form of employing these intermediates is through reaction of the ±-aminonitrile anion with different electrophiles. The use of ±-aminonitriles on ionic reactions has been widely explored in the last years; however, there are no reports of the use of radicals derived from these structures. One of the challenges on the use of these radicals is due to the high stability of these intermediates, due to the captodative effect. Photoredox catalysis has emerged as a good strategy in radical chemistry, since it is possible to generate radical intermediates under mild conditions, avoiding the use of high temperatures and stoichiometric radical initiators.This project aims to study the formation and reactivity of ±-aminonitriles radicals derived, as well as its subsequent use in functionalization reactions of heterocyclic compounds employing photoredox catalysis. (AU)