Effective Formation of New C(sp2)-S Bonds via Photoactivation of Alkylamine-based Electron Donor-Acceptor Complexes
[EN] A novel visible light promoted formation of CAryl-S bonds through electron donor-acceptor (EDA) complexes of alkylamines with 5- and 6-membered (hetero)arene halides is presented. This represents the first EDA-based thiolation method not relying on pi-pi or a thiolate-anion-pi interactions and...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2023 |
| País: | España |
| Institución: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:riunet.upv.es:10251/203409 |
| Acceso en línea: | https://riunet.upv.es/handle/10251/203409 |
| Access Level: | acceso abierto |
| Palabra clave: | EDA complex Heteroarene thiolation Single-electron transfer Sustainability Visible-light QUIMICA ORGANICA |
| Sumario: | [EN] A novel visible light promoted formation of CAryl-S bonds through electron donor-acceptor (EDA) complexes of alkylamines with 5- and 6-membered (hetero)arene halides is presented. This represents the first EDA-based thiolation method not relying on pi-pi or a thiolate-anion-pi interactions and provides a facile access to heteroarene radicals, which can be suitably trapped by disulfide derivatives to form the corresponding versatile arylsulfides. Mechanistic investigations on the aspects of the whole process were conducted by spectroscopic measurements, demonstrating the hypothesized EDA complex formation. Moreover, the strength of this method has been proven by a gram-scale synthesis of thiolated products and the late-stage derivatization of an anticoagulant drug. |
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