Organic Letters
Organic Letters
5 years ago

Construction of 1-Heteroaryl-3-azabicyclo[3.1.0]hexanes by sp3–sp2 Suzuki–Miyaura and Chan–Evans–Lam Coupling Reactions of Tertiary Trifluoroborates

Construction of 1-Heteroaryl-3-azabicyclo[3.1.0]hexanes by sp3–sp2 Suzuki–Miyaura and Chan–Evans–Lam Coupling Reactions of Tertiary Trifluoroborates
Michael R. Harris, Qifang Li, Jun Xiao, Yajing Lian, Allyn T. Londregan
Compounds that contain the 1-heteroaryl-3-azabicyclo[3.1.0]hexane architecture are of particular interest to the pharmaceutical industry yet remain a challenge to synthesize. We report herein an expedient and modular approach to the synthesis of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes by Suzuki–Miyaura and Chan–Evans–Lam coupling reactions of tertiary trifluoroborate salts. Our Suzuki–Miyaura cross-coupling protocol is compatible with a broad range of aryl and heteroaryl bromides and chlorides. The unprecedented Chan–Evans–Lam coupling of tertiary trifluoroborates allows the facile construction of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes containing C-tertiary arylamines at the ring juncture.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01097

DOI: 10.1021/acs.orglett.7b01097

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.