Litcius/Paper detail

New Radical Route and Insight for the Highly Efficient Synthesis of Benzimidazoles Integrated with Hydrogen Evolution

Yinfeng Wang, Ming‐Yu Qi, Marco Conte, Zi‐Rong Tang, Yi‐Jun Xu

2023Angewandte Chemie International Edition104 citationsDOIOpen Access PDF

Abstract

Abstract Benzimidazoles are a versatile class of scaffolds with important biological activities, whereas their synthesis in a lower‐cost and more efficient manner remains a challenge. Here, we demonstrate a conceptually new radical route for the high‐performance photoredox coupling of alcohols and diamines to synthesize benzimidazoles along with stoichiometric hydrogen (H 2 ) over Pd‐decorated ultrathin ZnO nanosheets (Pd/ZnO NSs). The mechanistic study reveals the unique advantage of ZnO NSs over other supports and particularly that the features of Pd nanoparticles in facilitating the cleavage of the α‐C−H bond of alcohols and adsorbing subsequently‐generated C‐centered radicals hold the key to turning on the reaction. This work highlights a new insight into radical‐induced efficient benzimidazole synthesis pairing with H 2 evolution by rationally designing semiconductor‐based photoredox systems.

Topics & Concepts

Combinatorial chemistryChemistryComputer scienceNanotechnologyMaterials scienceRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods