Development of a new methodologies for synthesis of bicyclic aromatic ketones and naphthols employing diazoketones and Beta-keto sulfoxonium ylides

• Grant number: 18/03667-0
• Support type: Scholarships in Brazil - Master
• Effective date (Start): July 01, 2018
• Effective date (End): August 31, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Cooperation agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Evandro de Azevedo Rocha
• Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

The Friedel-Crafts acylation reaction is one of the most important methods for the formation of aromatic ketones. There are several methodologies already described in the literature to obtain this class of compounds. However, these synthetic routes are very similar to the classical method developed by Friedel and Crafts, which use quite a number of supra-stoichiometric reactive Lewis or Brønsted acids, limiting the use of this methodology in multifunctionalized and / or sensitive substrates. Thus, it is proposed the development of a new methodology for the formation of bicyclic aromatic ketones through a synthetic route with few reactional steps and mild conditions. These compounds can be obtained by photochemical reaction in the presence of diazocarbonyl or sulfur ylides (compounds that act as precursors of ketene intermediates capable of promoting intramolecular cyclization similar to the traditional Friedel-Crafts reaction). (AU)