5 years ago

Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes

Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes
Marcus W. Drover, Jialing Geng, Addison N. Desnoyer, Brian O. Patrick, Jennifer A. Love
Low-valent nickel is shown to preferentially isomerize mono- or disubstituted epoxides into their corresponding aldehydes. Experiments with tetrasubstituted epoxides demonstrate that these reactions proceed via reactive 2-nickelaoxetane intermediates, and that the oxidative addition step likely occurs with retention of configuration. The monosubstituted aldehyde isomerization products were found to rapidly react with HBpin to form boronate esters. These hydroboration reactions could be performed catalytically. Nickel squares up: Low-valent nickel(0) is shown to isomerize styrenyl epoxides to aldehydes in high yields. Mechanistic studies indicate that these isomerizations occur via 2-nickelaoxetane intermediates. Catalytic hydroboration of styrene oxide with HBpin was also demonstrated to be facile.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702824

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.