3 years ago

Synthesis of Sulfur Perfluorophenyl Compounds Using a Pentafluorobenzenesulfonyl Hypervalent Iodonium Ylide

Synthesis of Sulfur Perfluorophenyl Compounds Using a Pentafluorobenzenesulfonyl Hypervalent Iodonium Ylide
Zhongyan Huang, Jiandong Wang, Shichong Jia, Norio Shibata, Etsuko Tokunaga, Kenta Okuyama, Yuji Sumii
A novel pentafluorobenzenesulfonyl hypervalent iodonium ylide 3 was designed and synthesized as a useful tool for the preparation of sulfur pentafluorophenyl compounds containing a C6F5S or C6F5SO2 unit. Electrophilic pentafluorophenylthiolation of enamines, formal [3+2] cycloaddition reaction of nitriles and alkynes, and intramolecular SNAr cyclization were achieved using iodonium ylide 3. The fluoro-click reaction was also demonstrated using one of the products via an intermolecular SNAr reaction with heterocentered nucleophiles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01908

DOI: 10.1021/acs.joc.7b01908

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.