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Synthesis of Sulfur-Containing Trisubstituted Imidazoles by One-Pot, Multicomponent Reaction via Electron Donor–Acceptor Complex Photoactivation

Junze Zuo, Xufeng Li, Yongjia Shi, Jian Lv, Daoshan Yang

2024Organic Letters43 citationsDOI

Abstract

Rapid and efficient construction of multifunctionalized skeletons through a one-pot multicompound domino reaction has been recognized as a simple and practical strategy. Herein, a visible-light-enabled three-component reaction of isothiocyanates, isocyanides, and thianthrenium salt-functionalized arenes is presented, which affords a facile approach to sulfur-containing trisubstituted imidazoles in good yields with a broad substrate scope and excellent functional group tolerance. The byproduct thianthrene is recovered in quantity, thereby ultimately reducing the production of chemical waste. The developed methodology has potential value for the discovery and development of thioimidazole-based drugs.

Topics & Concepts

ChemistrySulfurThianthreneCombinatorial chemistrySubstrate (aquarium)Cascade reactionFunctional groupReaction conditionsDominoAcceptorSalt (chemistry)Organic chemistryCatalysisCondensed matter physicsOceanographyGeologyPolymerPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Synthesis of Sulfur-Containing Trisubstituted Imidazoles by One-Pot, Multicomponent Reaction via Electron Donor–Acceptor Complex Photoactivation | Litcius