: A protocol exploiting isocyanides as carbamoylating agents for the α-C(sp3)-H functionalization of cyclic ethers has been optimized via a combined visible light-driven hydrogen atom transfer/Lewis acid-catalyzed approach. The isocyanide substrate scope revealed an exquisite functional group compatibility (18 examples, with yields up to 99 %). Both radical and polar trapping, kinetic isotopic effect and real-time NMR studies support the mechanistic hypothesis and provide insightful details for the design of new chemical processes involving the generation of oxocarbenium ions.
Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides / Russo, C.; Volpe, C.; Santoro, F.; Brancaccio, D.; Di Porzio, A.; Carotenuto, A.; Randazzo, A.; Grimaud, L.; Vitale, M. R.; Protti, S.; Giustiniano, M.. - In: CHEMISTRY. - ISSN 1521-3765. - 30:48(2024). [10.1002/chem.202401997]
Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides
Russo C.Primo
;Volpe C.;Santoro F.;Brancaccio D.;Di Porzio A.;Carotenuto A.;Randazzo A.;Giustiniano M.
2024
Abstract
: A protocol exploiting isocyanides as carbamoylating agents for the α-C(sp3)-H functionalization of cyclic ethers has been optimized via a combined visible light-driven hydrogen atom transfer/Lewis acid-catalyzed approach. The isocyanide substrate scope revealed an exquisite functional group compatibility (18 examples, with yields up to 99 %). Both radical and polar trapping, kinetic isotopic effect and real-time NMR studies support the mechanistic hypothesis and provide insightful details for the design of new chemical processes involving the generation of oxocarbenium ions.| File | Dimensione | Formato | |
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