Catalytic Desaturation of Aliphatic Amides and Imides Enabled by Excited-State Base-Metal Catalysis

Chenyang Wang, Luis Azofra Mesa, Phong Dam, Michael Sebek, Norbert Steinfeldt, Jabor Rabeah, Osama El-Sepelgy

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Herein, we report a photoexcited base-metal-catalyzed selective desaturation of aliphatic amides and imides. The reaction is catalyzed by a base-metal cobalt complex under visible-light irradiation. This transformation can be efficiently processed at room temperature and enables the synthesis of valuable cyclic and acyclic enamides and enimides from abundant chemicals. Density functional theory (DFT) analysis, electron paramagnetic resonance (EPR), and UV–vis studies rationalized the discovered reactivity of the cobalt catalyst for the photochemical C(sp3)–H activation reaction. Finally, we demonstrated the potential of our process by scaling-up experiments using a continuous flow photoreactor.
Original languageEnglish (US)
Pages (from-to)8868-8876
Number of pages9
JournalACS Catalysis
DOIs
StatePublished - Jul 10 2022
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2022-09-14
Acknowledgements: Prof. Dr. Matthias Beller is gratefully acknowledged for his continued generous support, and the paper is dedicated to him on the occasion of his 60th birthday. Gratitude is also due to KAUST for the use of supercomputer Shaheen II for providing the computational resources. This work was financially supported by Deutsche Forschungsgemeinschaft (DFG, Grant Number 456582392) and by the Leibniz Institute for Catalysis e.V.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

ASJC Scopus subject areas

  • Catalysis

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