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

Chemistry. 2023 Apr 18;29(22):e202300110. doi: 10.1002/chem.202300110. Epub 2023 Mar 9.

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.

Keywords: CuCl; alkynes; antifungal activities; green chemistry; photochemistry.

MeSH terms

  • Animals
  • Antifungal Agents* / chemistry
  • Catalysis
  • Chlorides
  • Copper* / chemistry
  • Halogens
  • Ketones / chemistry
  • Oxidation-Reduction
  • Temperature
  • Zebrafish

Substances

  • Antifungal Agents
  • Chlorides
  • Copper
  • Halogens
  • Ketones