Applications of the enantioselective Heck-Matsuda reaction in the synthesis of enantiomerically enriched indolines: methodological development and applications

• Grant number: 21/14403-6
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• Start date: June 01, 2022
• End date: February 28, 2023
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Otto Daolio Koster
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes, AP.TEM

Abstract

Considering the preliminary results from Prof. Correia's group, we aim at studying the intramolecular Heck Matsuda for the formation of indoline moieties. Based on methodologies under development in the research group for the in situ formation of arenediazonium compounds, the products can be synthesized directly from the anilines in a one-pot reaction. The in situ formation allows us to circumvent the difficulty of synthesizing and isolating some arenediazoniums salts, therefore, expanding the scope of substrates (anilines) for this reaction.Additional studies will be carried out to ensure the adequacy of arenediazonium salts formation in the presence of N, N-ligands, necessary for the adequate enantioselectivity of the reaction, thus enabling the synthesis of substituted indolines in high yields and enantiomeric excesses. (AU)