Greener C–H Arylation Reactions

  • ChemPubSoc Europe Logo
  • Author: Angewandte Chemie International Edition
  • Published Date: 18 February 2017
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Greener C–H Arylation Reactions

There have been attempts to develop catalytic arylation reactions using phenol and its simple derivatives instead of aryl halides. This would lead to more economical and "greener" chemical processes. The vast majority of efforts focused on developing cross-coupling reactions of inert phenol derivatives including aryl ethers, esters, and carbamates. These have involved the use of low-valent nickel catalysts. However, applications of such reactions to cross-coupling with C–H bonds have had only limited success.


Mamoru Tobisu, Naoto Chatani, Osaka University, Japan, and colleagues have established a protocol that permits aryl carbamates to be coupled to arene C–H bonds using a rhodium-based catalyst. The group developed a rhodium catalyst bearing two N-heterocyclic carbene (NHC) ligands, which can activate both an inert C(aryl)–O bond of an aryl carbamate and a C–H bond of an arene and catalyze cross-coupling reactions. The catalyst is generated in situ from [RhCl(C2H4)2]2 and a substituted NHC ligand. The reaction gives a range of biaryls (example pictured) in good to excellent yields.


 

Article Views: 1325

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