First Synthesis of N-Alkynylpyridinium Salts

  • Author: ChemistryViews.org
  • Published: 13 March 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: First Synthesis of <i>N</i>-Alkynylpyridinium Salts

Cationic nitrogen-embedded polycyclic aromatic hydrocarbons (cNe-PAHs) are compounds with interesting physicochemical properties and a variety of potential applications. Methods for the synthesis of cNe-PAHs can suffer from problems such as low regioselectivity and a limited product range. Using N-alkynylpyridinium salts (cation pictured) as precursors could help researchers to circumvent these issues.


Naoyuki Toriumi, University of Tokyo, Japan, Masanobu Uchiyama, University of Tokyo and RIKEN, Saitama, Japan, and colleagues have achieved the first synthesis of N-alkynylpyridinium salts. The team used alkynyl-λ3-iodanes as alkynyl transfer reagents to prepare the desired N-alkynylpyridinium cations from different pyridine derivatives in good to excellent yields.


The N-alkynylpyridinium cations are highly electrophilic and undergo Michael additions with hydrogen halides and thiols to give adducts in high yields. The team was then able to convert these products to the respective cNe-PAHs using intramolecular cyclization reactions. According to the researchers, the method can be used to prepare a variety of cNe-PAHs with interesting optical and electrochemical properties.


 

 

Article Views: 913

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