Preparation of propargyl halydes and allenes from propargylamines

• Grant number: 12/23145-1
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: February 01, 2013
• End date: June 30, 2013
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Alcindo Aparecido dos Santos
• Grantee: Felipe Ramos Neves
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

This project aims to apply A3-coupling reaction products (aldehydes, amines, and alkynes) as substrates on the preparation of propargyl halides, especially chlorides and allenes. The proposition is centered on the utilization of an electrophile able to react with a propargylamine through a nitrogen attack to the carbonyl carbon of an acid chloride derivative. From this reaction, an ammonium salt chloride is produced which can be capable to undergo a nucleophilic attack by the counterpart chloride ion. The same ammonium salt will be submitted to reaction in order to verify if is possible to be used as a substrate to prepare allenes and allenynes, by Pd catalysis. Chemometric tools will be used for the experimental rationalization. The development of this proposition is complementary to other projects under investigation in our group related to the regular FAPESP project (2011/613-8) and will contribute to the synthetic diversity of the A3-coupling-branch investigation of our group.(AU)