Nickel-Catalyzed Heteroarylation of Chiral Oxazolines

  • ChemPubSoc Europe Logo
  • Author: Andrei Dragan
  • Published Date: 24 September 2017
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Nickel-Catalyzed Heteroarylation of Chiral Oxazolines

Earth-abundant transition metals are preferred to noble metals because they are environmentally benign and have a lower cost. Nickel catalysts, for example, are attractive for organic synthesis

Inspired by nickel-catalyzed C–H bond functionalizations of oxazoles, Zhan Lu, Zhejiang University, Hangzhou, China, and colleagues have found that NiBr2 can efficiently catalyze C–H arylations of oxazolines. The team used NiBr2 together with 1,2-bis(diphenylphosphino)ethane (dppe) as a ligand in the presence of tBuOLi in toluene at 120 °C. Various aryl or heteroaryl halides (-Cl, -Br, -I) and oxazolines could be used as partners for the synthesis of chiral oxazoline-containing multidentate ligands (example pictured).

This method is particularly useful for the construction of the chiral oxazoline iminopyridine (OIP) ligand, which has been widely used in asymmetric hydrofunctionalizations of unsaturated C–C bonds or C–O double bonds. Moreover, a frequently used pybox ligand could be synthesized smoothly under these reaction conditions.


Article Views: 1561

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH