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. 2024 Aug 27;30(48):e202401997.
doi: 10.1002/chem.202401997. Epub 2024 Jul 31.

Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides

Camilla Russo  1 , Carmine Volpe  1 , Federica Santoro  1 , Diego Brancaccio  1 , Anna Di Porzio  1 , Alfonso Carotenuto  1 , Antonio Randazzo  1 , Laurence Grimaud  2 , Maxime R Vitale  2 , Stefano Protti  3 , Mariateresa Giustiniano  1
Affiliations

Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides

Camilla Russo et al. Chemistry. .

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.

Keywords: C−H carbamoylation; Hydrogen atom transfer; Isocyanides; Lewis acid catalysis; Radical polar crossover.

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