Visible-light-driven C-H functionalization of double bonds with diazo compounds under mild reaction conditions

Expanding the toolbox of C–H functionalization reactions applicable to the late-stage modification of complex molecules of interest in medicinal chemistry is a key strategy for drug development. Herein, we report an unusual visible-light-induced olefinic C(sp2)–H functionalization of olefins with di...

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Detalhes bibliográficos
Autores: Valle Amores, Miguel Angel, Carli, Benedetta, MacLean, Ian, Martínez-Fernández, Lara, Pérez-Ruíz, Raúl, Marzo Puerta, Leyre, Fraile Carrasco, Alberto, Alemán Lara, José Julián
Tipo de documento: artigo
Data de publicação:2026
País:España
Recursos:Universidad Autónoma de Madrid
Repositório:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglês
OAI Identifier:oai:dnet:biblosearchi::6093eacedef423908e59c33e3a2c605d
Acesso em linha:https://hdl.handle.net/10486/767620
https://dx.doi.org/10.1039/D5QO01537E
Access Level:Acceso aberto
Palavra-chave:Química
Descrição
Resumo:Expanding the toolbox of C–H functionalization reactions applicable to the late-stage modification of complex molecules of interest in medicinal chemistry is a key strategy for drug development. Herein, we report an unusual visible-light-induced olefinic C(sp2)–H functionalization of olefins with diazo derivatives using an Ir(III) photocatalyst. The approach demonstrates the potential for targeting double bonds, such as those present in enol ethers, and has been further applied to 1,1-disubstituted alkenes. This efficient methodology affords unprecedented Heck-type products in good to excellent yields under mild conditions. Further derivatizations of the final products are shown to demonstrate the robustness of the methodology. The reaction pathway was validated through electrochemical and photophysical experiments as well as computational studies