Organic Letters
Organic Letters
5 years ago

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products
David T. Smith, Jon T. Njardarson, Edon Vitaku
A mild dearomatization enabled ortho-selective replacement of an aromatic C–H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01479

DOI: 10.1021/acs.orglett.7b01479

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.