4 years ago

Recyclable Dirhodium(II) Catalyst Rh2(esp)2 for the Allylic Oxidation of Δ5-Steroids

Recyclable Dirhodium(II) Catalyst Rh2(esp)2 for the Allylic Oxidation of Δ5-Steroids
Yuanhua Wang, Yi Wang, Yi Kuang, Hongyang Zhang, Ruocheng Ma
The chelating dirhodium(II) catalyst Rh2(esp)2 was shown to efficiently catalyze the allylic oxidation of Δ5-steroids using T-HYDRO (70% tert-butyl hydroperoxide in water) as oxidant. Reaction yields were affected by the coordination ability of the solvent. The noncoordinating solvent n-heptane was determined to be an optimal solvent. At gram scale, the product, Δ5-en-7-one steroid, precipitated from the reaction mixture. The Rh2(esp)2 complex did not undergo catalytic degradation and was recycled using Merrifield–pyridine resin for further allylic oxidation cycles. The results of ultraviolet/visible spectral analysis suggested that the Rh2(II,II) species, rather than the Rh2(II,III) species, was in the catalyst resting state during the reaction, which helps to explain the high durability of the catalyst.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00414

DOI: 10.1021/acs.joc.7b00414

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.