Alkenylation of Pyridylmethylesters

  • Author:
  • Published: 12 May 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Alkenylation of Pyridylmethylesters

Vinylations of organic compounds are useful synthetic transformations. Coupling nucleophiles with vinyl halides can introduce β,γ-unsaturated groups in an efficient way. However, transition-metal catalyzed reactions of this type have been limited mostly to enolate and nitronate substrates.

Xiaodong Yang, Patrick J. Walsh, and colleagues, University of Pennsylvania, Philadelphia, USA, have developed a palladium-catalyzed α-alkenylation of pyridylmethyl ethers with vinyl bromides (product pictured). The team uses a Pd–NIXANTPHOS catalyst (NIXANTPHOS = 4,6-bis(diphenylphosphino)phenoxazine), together with LiN(SiMe3)2 as a base and cyclopentyl methyl ether (CPME) as a solvent.

The reaction proceeded under mild conditions (65 °C over 12 hours), and the team was able to couple a variety of pyridylmethyl ethers with a range of vinyl bromides. The yields were good to excellent (up to 97 %). The researchers are working on a catalyst for an enantioselective variant of the reaction.


Article Views: 1602

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