Ruthenium-Catalyzed Allylation of Indoles

  • Author: ChemistryViews.org
  • Published: 30 March 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Ruthenium-Catalyzed Allylation of Indoles

Allyl arenes are useful synthetic intermediates. Their synthesis usually involves methods with limited substrate scopes and/or harsh reaction conditions.


Xiaowei Wu, H. Lee Moffitt Cancer Center and Research Institute, Tampa, FL, USA, Haitao Ji, H. Lee Moffitt Cancer Center and Research Institute and University of South Florida, Tampa, USA, have developed a ruthenium-catalyzed allylation of indoles under mild conditions that tolerates a range of functional groups. The team used [{RuCl2(p-cymene)}2] as a catalyst and sodium acetate as a base to couple a variety of indoles featuring an N-ethoxycarbamoyl directing group with allyl alcohols in methanol at 45 °C (example product pictured).


The reaction proceeds via a β-hydroxide elimination and has good to excellent regio- and stereoselectivity. The method tolerates both electron-donating and electron-withdrawing substituents at the indole and the allyl alcohol.


 

Article Views: 1688

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

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH