{"title":"Iron(II) triflate as a photocatalyst for trifluoromethylation of functionalized arenes under blue LED light: Access to bioactive compounds","authors":"Sandeep Kumawat, Kishore Natte","doi":"10.1016/j.jcat.2024.115506","DOIUrl":null,"url":null,"abstract":"<div><p>The trifluoromethyl group (-CF<sub>3</sub>) containing motifs are valuable leads for the small molecule drug discovery process and have multiple applications in medicine, agriculture, and material science. Not many CF<sub>3</sub>-containing motifs are commercially accessible; therefore, it is critical to design more advanced building blocks. In this work, we demonstrate an oxidant-free, scalable, and user-friendly protocol for the direct C(sp<sup>2</sup>)-H trifluoromethylation of functionalized arenes using Iron(II) triflate as a robust photocatalyst and bench-stable CF<sub>3</sub>SO<sub>2</sub>Na (1.5 equiv.) as a CF<sub>3</sub> source under blue light irradiation. This method was extrapolated to >30 examples and compatible with potential functional groups (-NO<sub>2</sub>, -NH<sub>2</sub>, OH, -CHO, -CO<sub>2</sub>H, halogens, etc.). Notably, the utility of this approach is showcased for the synthesis of novel CF<sub>3</sub>-containing synthetic building blocks and a few bioactive compounds.</p></div>","PeriodicalId":346,"journal":{"name":"Journal of Catalysis","volume":null,"pages":null},"PeriodicalIF":6.5000,"publicationDate":"2024-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0021951724002197","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
The trifluoromethyl group (-CF3) containing motifs are valuable leads for the small molecule drug discovery process and have multiple applications in medicine, agriculture, and material science. Not many CF3-containing motifs are commercially accessible; therefore, it is critical to design more advanced building blocks. In this work, we demonstrate an oxidant-free, scalable, and user-friendly protocol for the direct C(sp2)-H trifluoromethylation of functionalized arenes using Iron(II) triflate as a robust photocatalyst and bench-stable CF3SO2Na (1.5 equiv.) as a CF3 source under blue light irradiation. This method was extrapolated to >30 examples and compatible with potential functional groups (-NO2, -NH2, OH, -CHO, -CO2H, halogens, etc.). Notably, the utility of this approach is showcased for the synthesis of novel CF3-containing synthetic building blocks and a few bioactive compounds.
期刊介绍：
The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes.
The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods.
The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.
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