3 years ago

Radical Trifluoromethylative Dearomatization of Indoles and Furans with CO2

Radical Trifluoromethylative Dearomatization of Indoles and Furans with CO2
Si-Shun Yan, Meng Miao, Lei Zhu, Xin-Chi Zhang, Wen-Jun Zhou, Yu Lan, Jing Li, Da-Gang Yu, Jian-Heng Ye
Disclosed herein is a versatile and practical strategy for catalytic radical dearomatization. By means of this strategy, we realized the trifluoromethylative dearomatization of indoles and furans with CO2 via Cu catalysis. We also demonstrated the dearomatization of indoles with C-3 C–O bond formation to generate spirocyclic indolines. A variety of important CF3-containing spirocyclic indolines and spiroacetals can be synthesized with atmospheric CO2 under mild reaction conditions. Moreover, these multicomponent reactions feature high selectivity, good functional group tolerance, broad substrate scope, and easy scalability. Further theoretical investigation indicates that this transformation starts with deprotonation of the amine and CO2 insertion, after which CF3· radical addition to the indole followed by intramolecular C–O coupling affords the oxazolidone product.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02533

DOI: 10.1021/acscatal.7b02533

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.