Photoredox-Catalyzed Alkenylation of Organosulfur Compounds

  • ChemPubSoc Europe Logo
  • Author: Chemistry – An Asian Journal
  • Published Date: 12 February 2019
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Photoredox-Catalyzed Alkenylation of Organosulfur Compounds

The Mizoroki–Heck reaction is an alkenylation reaction of organic halides using alkenes. The alkenylation of organosulfur compounds instead of organic halides is challenging due to the catalyst-poisoning nature of the anionic sulfur species generated in the course of the reaction.


Hideki Yorimitsu, Kyoto University, Japan, and colleagues have developed a photoredox-catalyzed alkenylation of benzylsulfonium salts via cleavage of their C–S bonds. The team used fac-Ir(ppy)3 (ppy = 2-phenylpyridine) as a catalyst, Na2CO3 as a base, and N-methylpyrrolidone as a solvent to react several benzylsulfonium salts (pictured left) and styrenes (pictured right) under blue light-emitting diode (LED) irradiation. The benzylsulfonium reactants can be readily prepared from the corresponding benzyl alcohols.


The desired allylbenzene products were obtained in moderate to good yields. The leaving groups are neutral sulfides, which do not poison the catalyst as easily as anionic species. The reaction tolerates a variety of functional groups, such as halogen, ester, and cyano groups.


 

Article Views: 704

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