δ-Amination of alkyl alcohols via energy transfer photocatalysis
Amino alcohols play a crucial role in the realm of biologically active compounds due to their functional diversity. In this study, we introduce a metal-free energy transfer photocatalytic method for the preparation of 1,4-aminoalcohols from readily available alcohol feedstocks. The key feature of th...
| Autores: | , , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Recursos: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/716920 |
| Acesso em linha: | http://hdl.handle.net/10486/716920 https://dx.doi.org/10.1039/D4QO01522C |
| Access Level: | acceso abierto |
| Palavra-chave: | Amination Amines Carboxylation Photocatalytic Activity Química |
| Resumo: | Amino alcohols play a crucial role in the realm of biologically active compounds due to their functional diversity. In this study, we introduce a metal-free energy transfer photocatalytic method for the preparation of 1,4-aminoalcohols from readily available alcohol feedstocks. The key feature of this transformation is the simultaneous generation of a persistent iminyl radical and a transient carbon-centered radical through σ-homolytic cleavage of the O–N bond via energy transfer (EnT). The process involves fragmentation/decarboxylation/1,5-HAT (hydrogen atom transfer), leading to the formation of a C(sp3)-hybridized radical, which undergoes selective radical–radical cross-coupling or a radical chain event to yield the desired products. In addition, the protocol was also found to be suitable for N-tosyl amines, giving rise to 1,4-diamines. Our approach combines experimental mechanistic investigations with detailed computational studies using density functional theory (DFT) to provide insights into the reaction mechanism. This innovative method provides a new approach for preparing δ-amino alkyl alcohols and amines |
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