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Copper (I) Chloride‐Catalyzed Photoredox Synthesis of Multifunctionalized Compounds at Room Temperature and Their Antifungal Activities

Vaibhav Pramod Charpe, Ayyakkannu Ragupathi, Arunachalam Sagadevan, Yeu‐Shiuan Ho, Mu‐Jeng Cheng, Kuo Chu Hwang

2023Chemistry - A European Journal15 citationsDOI

Abstract

A simple visible-light-induced CuCl-catalyzed synthesis was developed for highly functionalized carbon-centered compounds (α-alk/aryloxy-α-diaryl/alkylaryl-acetaldehydes/ketones) at room temperature using benzoquinone, alkyl/aryl alcohol, and alkyl/aryl terminal/internal alkynes. Late-stage functionalized compounds show good antifungal activities, especially against Candida krusei fungal strain, in in vitro experiments (the Broth microdilution method). Moreover, toxicity tests (zebrafish egg model experiments) indicated that these compounds had negligible cytotoxicity. The green chemistry metrics (E-factor value is 7.3) and eco-scale (eco-scale value is 58.8) evaluations show that the method is simple, mild, highly efficient, eco-friendly, and environmentally feasible.

Topics & Concepts

AlkylArylChemistryCatalysisOrganic chemistryAlcoholAntifungalCombinatorial chemistryMicrobiologyBiologyCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions