3 years ago

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
Pei Zhang, Haigen Shen, Xinqiang Tan, Chaozhong Li, Zhonglin Liu, Zhenzhen Zhang
The silver-catalyzed decarboxylative trifluoromethylation of aliphatic carboxylic acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic carboxylic acids with (bpy)Cu(CF3)3 (bpy = 2,2′-bipyridine) and ZnMe2 in aqueous acetonitrile at 40 °C afford the corresponding decarboxylative trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl carboxylic acids and exhibits wide functional group compatibility. Mechanistic studies reveal the intermediacy of Cu(CF3)3Me, which undergoes reductive elimination and subsequent oxidation to give Cu(CF3)2 as the active species responsible for the trifluoromethylation of alkyl radicals.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07944

DOI: 10.1021/jacs.7b07944

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.