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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides
Camilla Russo1, Carmine Volpe1, Federica Santoro1
1Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
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.
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