Water-Promoted Carbon-Carbon Bond Cleavage Employing a Reusable Fe Single-Atom Catalyst

Haifeng Qi, Shuxin Mao, Jabor Rabeah, Ruiyang Qu, Na Yang, Zupeng Chen, Florian Bourriquen, Ji Yang, Jianfeng Li, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The development of methods for selective cleavage reactions of thermodynamically stable C−C/C=C bonds in a green manner is a challenging research field which is largely unexplored. Herein, we present a heterogeneous Fe−N−C catalyst with highly dispersed iron centers that allows for the oxidative C−C/C=C bond cleavage of amines, secondary alcohols, ketones, and olefins in the presence of air (O2) and water (H2O). Mechanistic studies reveal the presence of water to be essential for the performance of the Fe−N−C system, boosting the product yield from <1 % to >90 %. Combined spectroscopic characterizations and control experiments suggest the singlet 1O2 and hydroxide species generated from O2 and H2O, respectively, take selectively part in the C−C bond cleavage. The broad applicability (>40 examples) even for complex drugs as well as high activity, selectivity, and durability under comparably mild conditions highlight this unique catalytic system.

Original languageEnglish
Article numbere202311913
JournalAngewandte Chemie International Edition in English
Volume62
Issue number43
DOIs
StatePublished - 23 Oct 2023
Externally publishedYes

Keywords

  • Amide
  • Amine
  • Iron
  • Singlet Oxygen
  • Water

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