Litcius/Paper detail

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, Jian‐Feng Li, Kathrin Junge, Matthias Beller

2023Angewandte Chemie International Edition33 citationsDOIOpen Access PDF

Abstract

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 (O 2 ) and water (H 2 O). 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 1 O 2 and hydroxide species generated from O 2 and H 2 O, 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.

Topics & Concepts

CatalysisBond cleavageCleavage (geology)ChemistrySelectivityHydroxidePhotochemistryInorganic chemistryOrganic chemistryMaterials scienceFracture (geology)Composite materialAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsNanomaterials for catalytic reactions