O-H bond activation of β,γ-unsaturated oximes via hydrogen atom transfer (HAT) and photoredox dual catalysis

Liang Yi, Chen Zhu, Xiangyu Chen, Huifeng Yue, Tengfei Ji, Yiqiao Ma, Yuanyuan Cao, Rajesh Kancherla, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Hydrogen atom transfer (HAT) and photoredox dual catalysis provides a unique opportunity in organic synthesis, enabling the direct activation of C/Si/S-H bonds. However, the activation of O-H bonds of β,γ-unsaturated oximes poses a challenge due to their relatively high redox potential, which exceeds the oxidizing capacity of most currently developed photocatalysts. We here demonstrate that the combination of HAT and photoredox catalysis allows the activation of O-H bond of β,γ-unsaturated oximes. The strategy effectively addresses the oxime's high redox potential and offers a universal pathway for iminoxyl radical formation. Leveraging the versatility of this approach, a diverse array of valuable heterocycles have been synthesized with the use of different radical acceptors. Mechanistic studies confirm a HAT process for the O-H bond activation.

Original languageEnglish (US)
Pages (from-to)14271-14279
Number of pages9
JournalChemical Science
Volume14
Issue number48
DOIs
StatePublished - Nov 30 2023

ASJC Scopus subject areas

  • General Chemistry

Fingerprint

Dive into the research topics of 'O-H bond activation of β,γ-unsaturated oximes via hydrogen atom transfer (HAT) and photoredox dual catalysis'. Together they form a unique fingerprint.

Cite this