Direct Synthesis of Tetrahydroquinolines

  • Author: European Journal of Organic Chemistry
  • Published Date: 19 June 2019
  • Source / Publisher: European Journal of Organic Chemistry//Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Direct Synthesis of Tetrahydroquinolines

Related Societies

Aromatic amines are commonly found in natural products, drugs, and dyes. Traditionally, they were prepared in multi-step sequences from nitroaromatics. More recently, metal-catalyzed amination of aromatic halides e.g. Buchwald-Hartwig (Pd) and Ullmann (Cu) couplings have been widely adopted, particularly in the pharmaceutical industry. A potentially more efficient approach would be to directly replace a C–H bond on an aromatic molecule with an amine of interest.

Steve Marsden, University of Leeds, UK, and colleagues have developed such a method for the direct synthesis of tetrahydroquinolines (pictured above). The aromatic C–H bonds are aminated by highly reactive aminium radicals. These are generated from readily-available N-chloroamines under catalysis by earth-abundant iron salts and CH2Cl2 as solvent.



Importantly, the chloroamine formation and aromatic amination can be carried out sequentially in a single reaction vessel, allowing for direct conversion of amines to arylated derivatives.


Article Views: 1299

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, 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