Organic halides play a key role as building blocks in synthesis because of their low cost and wide availability. In recent years, halogen-atom transfer (XAT) has emerged as a reliable approach to exploit these substrates in radical processes. Herein, we report a hydroalkylation of electron-poor olefins using alkyl bromides based on a UVA-induced silane-mediated XAT reaction. Our protocol is operationally simple, displays a broad scope and does not require a photocatalyst. Flow technology was used to reduce the reaction times and scale the process. Notably, a two-step protocol, combining the XAT protocol with a subsequent Horner-Wadsworth-Emmons reaction, has been developed to enable the allylation of C(sp3)–Br bonds.
Flow photochemical Giese reaction via silane-mediated activation of alkyl bromides / Fanini, F., Luridiana, A., Mazzarella, D., Alfano, A.I., van der Heide, P., Rincón, J.A., García-Losada, P., Mateos, C., Frederick, M.O., Nuño, M., Noel, T.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 117:(2023). [10.1016/j.tetlet.2023.154380]
Flow photochemical Giese reaction via silane-mediated activation of alkyl bromides
Antonella Ilenia Alfano;
2023
Abstract
Organic halides play a key role as building blocks in synthesis because of their low cost and wide availability. In recent years, halogen-atom transfer (XAT) has emerged as a reliable approach to exploit these substrates in radical processes. Herein, we report a hydroalkylation of electron-poor olefins using alkyl bromides based on a UVA-induced silane-mediated XAT reaction. Our protocol is operationally simple, displays a broad scope and does not require a photocatalyst. Flow technology was used to reduce the reaction times and scale the process. Notably, a two-step protocol, combining the XAT protocol with a subsequent Horner-Wadsworth-Emmons reaction, has been developed to enable the allylation of C(sp3)–Br bonds.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
