Organic Letters
Organic Letters
5 years ago

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines
Yan-dong Wu, An-xin Wu, Xiao Geng, Xia Wu, Peng Zhao
The iodine-catalyzed catalytic formal [3 + 3 + 1] cycloaddition for the preparation of a seven-membered O-heterocyclic ring is presented, which is an achievement of methyl and carbonyl group reactivity of 3-methyl-5-pyrazolones to forge the Csp3–O bond. This novel protocol provides a straightforward and efficient access to structurally diverse fused O-heterocycles through an iodine-catalyzed iodination/Kornblum oxidation/oxidative coupling/C–O bond formation cascade reaction. This approach demonstrates the unprecedented concurrent realization of the unique reactivity among the methyl, methylene, and carbonyl groups in 3-methyl-5-pyrazolones for the construction of 2,3-dihydrooxepine rings. Moreover, a broad substrate scope displays a graceful diversity-oriented synthetic approach.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02182

DOI: 10.1021/acs.orglett.7b02182

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.