CuH-catalyzed hydrofluorination of aryl alkenes

• Grant number: 18/23115-1
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• Start date: July 01, 2019
• End date: June 30, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Carlos Henrique Alves Esteves
• Supervisor: Stephen L. Buchwald
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Institution abroad: Massachusetts Institute of Technology (MIT), United States
• Associated to the scholarship: 17/26673-2 - CuH-Catalyzed fluorination of alkenes and PET applications, BP.PD

Abstract

The fluorination of organic compounds has become a hot topic in the chemical literature due to the increasing importance of fluorinated molecules, especially in the pharmaceutical industry where they account for 30% of all recently approved drugs. The present proposal details an approach to the enantioselective fluorination of readily available aryl alkenes relying on copper-hydride catalysis. This concept has successfully permitted a variety of enantioselective functionalizations of alkenes such as hydroamination, hydrosilylation, hydroboration and hydroamidation. In this context, the development of an enantioselective hydrofluorination reaction would greatly contribute to the development of the field of fluorine chemistry, introducing a methodology to construct tertiary fluorinated chiral centers, a chemical architecture currently hard to obtain via established protocols. (AU)