Visible Light‐promoted C(<i>sp</i><sup>3</sup>)‐H α‐Carbamoylation of Cyclic Ethers with Isocyanides-Reference-Cited by-同舟云学术

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

Published:2024-07-31 Issue:48 Volume:30 Page:
ISSN:0947-6539
Container-title:Chemistry – A European Journal
language:en
Short-container-title:Chemistry A European J

Author:

Russo Camilla¹,Volpe Carmine¹,Santoro Federica¹,Brancaccio Diego¹,Di Porzio Anna¹,Carotenuto Alfonso¹,Randazzo Antonio¹,Grimaud Laurence²,Vitale Maxime R.²,Protti Stefano³,Giustiniano Mariateresa¹^ORCID

Affiliation:

1. Department of Pharmacy University of Naples Federico II via D. Montesano 49 80131 Napoli Italy

2. Laboratoire des Biomolécules (LBM) Département de Chimie École Normale Supérieure PSL University, Sorbonne Université, CNRS 75005 Paris France

3. PhotoGreenLab Department of Chemistry University of Pavia viale Taramelli 12 27100 Pavia Italy

Abstract

AbstractA 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.

Funder

Università Italo Francese

Ministero dell'Università e della Ricerca

Publisher

Wiley

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