3 years ago

Manganese(I)-Catalyzed Regioselective C−H Allenylation: Direct Access to 2-Allenylindoles

Manganese(I)-Catalyzed Regioselective C−H Allenylation: Direct Access to 2-Allenylindoles
Frank Glorius, Steffen Greßies, Felix J. R. Klauck, Qingquan Lu
A MnI-catalyzed regioselective C−H allenylation is reported that allows a broad range of 2-allenylindoles to be synthesized regioselectively on a gram scale under simple conditions. Notably, a highly efficient chirality transfer was observed (up to 93 % ee) in this transformation. This procedure was further found to allow, for the first time, the direct preparation of ketones by MnI-catalyzed C−H activation. Mechanistic investigations revealed that the precoordination of the oxygen atom to the manganese center as well as the congested tertiary carbon atom in the propargylic carbonates play a crucial role. Magic manganese! The title reaction allows simple access to a broad range of 2-allenylindoles with efficient chirality transfer, and for the first time also allows the direct preparation of ketones by MnI-catalyzed C−H activation. The coordination of the carbonate oxygen atom to the Mn catalyst and the congested tertiary carbon atom play crucial roles in the reaction mechanism.

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

DOI: 10.1002/anie.201701767

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.