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

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 function...

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Veröffentlicht in:Chemistry : a European journal 2023-04, Vol.29 (22), p.e202300110-n/a
Hauptverfasser: Charpe, Vaibhav Pramod, Ragupathi, Ayyakkannu, Sagadevan, Arunachalam, Ho, Yeu‐Shiuan, Cheng, Mu‐Jeng, Hwang, Kuo Chu
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Sprache:eng
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Zusammenfassung: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. A mild and highly efficient copper photoredox‐catalyzed three‐component coupling of BQ, alkyl/aryl alcohols, and alkyl/aryl terminal/internal alkynes forms highly functionalized products at room temperature. The late‐stage functionalized compounds show good anti‐Candida krusei and anti‐Candida glabrata activities with lower cytotoxicities than that of fluconazole, the standard antifungal medicine.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202300110