New synthetic applications of the Heck arylations using arenediazonium salts

• Grant number: 08/03317-7
• Support Opportunities: Regular Research Grants
• Start date: October 01, 2008
• End date: September 30, 2011
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Carlos Roque Duarte Correia
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The proposal is divided into 3 projects. Project I has as its main objective the study of the Heck arylations of maleic anhydrides and maleimides employing arenediazonium salts to produce molecular probes possessing strong fluorescence. These compounds are important tracking devices in biological systems which have been attracting a lot of attention of the scientific community nowadays. Other objectives of this subproject I are the synthesis of new, and structurally simpler analogues of the antitumoral antibiotic rebecamicina, together with the total synthesis of the marine alkaloid polycitrine B. Project II has as its objectives to apply the Heck arylations with arenediazonium salts for the total synthesis of the antitumoral catequins, a commun component of the green tea, as well as the total synthesis of the flavonoid compound luteoline. Project III uses the same Heck arylation approach employing arenediazonium salts in the synthesis of arylprolines and arylkainoid compounds with potential to perform as effective organocatalysts. This is an area of intense activity nowadays and our own experience in this field has demonstrated that new arylprolines can actually perform as organocatalysts and new ligands for use in enantioselective catalysis using organometallic complexes.Each project focus on one type of olefin, therefore project I use a electronically deficient olefin, whereas project II relies on electronically rich olefins. Project III on the other hand features a Heck arylation of a non-activated olefin as key synthetic element.The proposal was elaborated as a challenging synthetic strategy to provide all the necessary ingredients for the development of scientific expertise of MSc and PhD students, as well as pos-docs and young new undergraduate students. (AU)