Functionalization of halogen-substituted benzonitriles using the organometallic base TMPMgCl.LiCl

• Grant number: 15/24034-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Effective date (Start): February 01, 2016
• Effective date (End): January 31, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Giuliano Cesar Clososki
• Grantee: Angela da Silva Santos
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil

Abstract

Magnesium and zinc organometallic bases complexed with lithium chloride were recently introduced in the literature and demonstrated great potential in the functionalization of various aromatics and heterocyclic rings. However, its reactivity towards important substrates has not yet been properly studied. This is the case of the nitrile unit, which although have find a large and wide range of applications in organic synthesis, received little attention from researchers working in the area. Thus, the main objective of this project is to develop methodologies for the preparation of high functionalized benzonitriles using the organometallic base TMPMgCl.LiCl that could be applied in the synthesis of bioactive molecules. In order to obtain biarylated derivatives, Negishi cross-coupling reactions will be performed. These reactions are still an important tool for the formation of carbon-carbon bonds and also in the functionalization of organic compounds. In addition, the novel nitriles to be synthesized in this project will be tested by the Faculty of groups engaged in the biological assessment of natural and synthetic substances.