Tris(trimethylsilyl)silane and visible-light irradiation : a new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

• Ano de defesa: 2016
• Autor(a) principal: Silva, Gustavo Piva da
• Orientador(a): Paixão, Márcio Weber
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: eng
• Instituição de defesa: Universidade Federal de São Carlos; Câmpus São Carlos
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química - PPGQ
• Palavras-chave em Inglês: Indole; Oxindole; Photochemistry
• Área do conhecimento CNPq: CIENCIAS EXATAS E DA TERRA::QUIMICA; CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
• Link de acesso: https://repositorio.ufscar.br/handle/20.500.14289/8610

A combined tris(trimethylsilyl)silane and visible-light-promoted intramolecular reductive cyclization protocol for the synthesis of indoles and oxindoles has been developed (Scheme 1).1 This straightforward and efficient protocol shows a broad functional-group tolerance and enables rapid and practical synthesis of functionalized nitrogen-based heterocycles in high/moderate yields under additive and metal-free, mild photochemical conditions. Besides the synthetic developments, the reaction mechanism was also investigated by a set of controlled experiments and UVvisible analyses, as well as kinetic study.2 From these studies, we have concluded that the reaction pathway for this strategy occurs through an Electron Donor-Acceptor (EDA) complex.3 to be continued ...