Estudo da aplicação de brometo de índio(I) em reações para formação de ligações carbono-carbono

• Ano de defesa: 2011
• Autor(a) principal: Chagas, Rafael Pavão das
• Tipo de documento: Tese
• Tipo de acesso: Acesso aberto
• dARK ID: ark:/26339/001300000jvtg
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; BR; Química; UFSM; Programa de Pós-Graduação em Química
• Palavras-chave em Português: Brometo de índio(I); Enolato de índio; Organoíndio; Reação aldólica; Ciclopropanação; Formação de ligações carbono-carbono; Indium(I) bromide; Indium enolate; Organoindium; Aldol reaction; Cyclopropanation; Carbon-carbon bond formation; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/4206

This PhD thesis describes our results on the application of indium(I) bromide in carbon-carbon bond forming reactions. Indium enolates, generated in situ from the reaction between indium(I) bromide and α,α-dichloroketones, react with carbonyl compounds and electron-deficient alkenes. Reactions of indium enolate with α,α-dichloroketones, in presence of extra InBr, leads to the formation of 1,4-diketones. The coupling with aldehydes leads alternatively, according as the stoichiometry, to the diastereoselective synthesis of (syn+anti)-2-chloro-3-hydroxy-propan-1-ones (which can be converted to the respective trans-epoxyketones), (E)-α,β-unsaturated ketones and cyclopropanes, upon a sequenced reaction mechanism. We also have developed a methodology for the preparation of cyclopropanes through the reaction of the indium enolate and other organoindium(III) compounds, derived from the reactions between InBr and α,α-dihalo carbonyl compounds and halo-acetonitriles, with electron-deficient alkenes.