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Visible Light-promoted C(sp3)-H α-Carbamoylation of Cyclic Ethers with Isocyanides.
Russo, Camilla; Volpe, Carmine; Santoro, Federica; Brancaccio, Diego; Di Porzio, Anna; Carotenuto, Alfonso; Randazzo, Antonio; Grimaud, Laurence; Vitale, Maxime R; Protti, Stefano; Giustiniano, Mariateresa.
Afiliação
  • Russo C; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Volpe C; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Santoro F; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Brancaccio D; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Di Porzio A; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Carotenuto A; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Randazzo A; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
  • Grimaud L; Laboratoire des Biomolécules (LBM), Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 75005, Paris, France.
  • Vitale MR; Laboratoire des Biomolécules (LBM), Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 75005, Paris, France.
  • Protti S; PhotoGreenLab, Department of Chemistry, University of Pavia, viale Taramelli 12, 27100, Pavia, Italy.
  • Giustiniano M; Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
Chemistry ; : e202401997, 2024 Jun 14.
Article em En | MEDLINE | ID: mdl-38873846
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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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article