Halogenações biomiméticas de compostos aromáticos e heteroaromaticos
Data
2022
Autores
Rita, Bruno Henrique 
Orientadores
Raminelli, Cristiano
Tipo
Dissertação de mestrado
Título da Revista
ISSN da Revista
Título de Volume
Resumo
Compostos orgânicos halogenados podem ser considerados blocos de construção versáteis em síntese orgânica, com aplicação em sínteses totais de produtos naturais e na produção de polímeros com propriedades variadas. Além disso, um número considerável de compostos orgânicos halogenados são fármacos atualmente comercializados ou substâncias de importância em medicina. Consequentemente, o desenvolvimento de métodos para halofuncionalizações de substâncias orgânicas tem lugar de destaque em química orgânica preparativa. Neste contexto, ampliamos o escopo de nossa reação de iodofuncionalização biomimética de compostos aromáticos e heteroaromáticos, empregando o sistema NaX/H2O2 (30%) (X = Cl e Br), fazendo uso de SeCl4 como catalisador e água destilada como solvente, obtendo compostos aromáticos e heteroaromáticos mono- e dibromados, em rendimentos entre 13% e 95%. As reações de cloração não resultaram nos compostos de interesse. Adicionalmente, experimentos de RMN de 77Se foram realizados, visando dar suporte experimental ao mecanismo proposto, para as reações de halofuncionalização desenvolvidas em nosso grupo de pesquisa.
Halogenated organic compounds can be considered versatile building blocks in organic synthesis, with application in total syntheses of natural products and in the production of polymers with varied properties. In addition, a considerable number of halogenated organic compounds are currently marketed drugs or substances of importance in medicine. Consequently, the development of methods for halofunctionalizations of organic substances has a prominent place in preparative organic chemistry. In this context, we broadened the scope of our biomimetic iodofunctionalization reaction of aromatic and heteroaromatic compounds, using the NaX/H2O2 (30%) system (X = Cl and Br), using SeCl4 as catalyst and distilled water as solvent, obtaining mono- and dibrominated aromatic and heteroaromatic compounds, in yields between 13% and 95%. The chlorination reactions did not result in the compounds of interest. Additionally, 77Se NMR experiments were performed, aiming to give experimental support to the proposed mechanism for the halofunctionalization reactions developed in our research group.
Halogenated organic compounds can be considered versatile building blocks in organic synthesis, with application in total syntheses of natural products and in the production of polymers with varied properties. In addition, a considerable number of halogenated organic compounds are currently marketed drugs or substances of importance in medicine. Consequently, the development of methods for halofunctionalizations of organic substances has a prominent place in preparative organic chemistry. In this context, we broadened the scope of our biomimetic iodofunctionalization reaction of aromatic and heteroaromatic compounds, using the NaX/H2O2 (30%) system (X = Cl and Br), using SeCl4 as catalyst and distilled water as solvent, obtaining mono- and dibrominated aromatic and heteroaromatic compounds, in yields between 13% and 95%. The chlorination reactions did not result in the compounds of interest. Additionally, 77Se NMR experiments were performed, aiming to give experimental support to the proposed mechanism for the halofunctionalization reactions developed in our research group.