Manganese-Catalyzed Synthesis of Allylated Arenes

  • Author: ChemistryViews.org
  • Published: 10 October 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Manganese-Catalyzed Synthesis of Allylated Arenes

Polysubstituted allyl groups, such as the prenyl group, are useful in synthetic intermediates. They can also be found in bioactive compounds, particularly in prenylated arenes or heteroarenes. Existing processes for the synthesis of prenylated arenes can suffer from poor atom economy, harsh reaction conditions, or a need for expensive noble metal catalysts.


Honggen Wang, Sun Yat-sen University, Guangzhou, China, Qingjiang Li, Sun Yat-sen University and Peking University, Beijing, China, and colleagues have developed a manganese(I)-catalyzed coupling of arenes with allenes to introduce prenyl groups and other polysubstituted allyl groups. The team combined a variety of indoles with different polysubstituted allenes, using [MnBr(CO)5] as a catalyst, NaOAc as an additive, and 1,4-dioxane as the solvent at 100 °C. The reaction gave the desired allylated arenes (example pictured) in good to excellent yields.


The researchers were able to upscale the atom-economic synthesis to a gram scale while using a low catalyst loading (2.5 mol%). According to the team, the method could have applications in the synthesis of bioactive natural products and medicinal chemistry.



Also of Interest

 

Article Views: 658

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 ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


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