Alkynylation of Aryl Carbamates

  • Author:
  • Published: 03 April 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Alkynylation of Aryl Carbamates

Alkynes are useful intermediates in organic synthesis. Often, alkynes are prepared using coupling reactions with organometallic nucleophiles. However, these strong nucleophiles limit the reactions' functional group tolerance.

Kosuke Yasui, Naoto Chatani, and Mamoru Tobisu, Osaka University, Japan, have developed a rhodium-catalyzed alkynylation of aryl carbamates that avoids this problem by using propargyl alcohols as the alkynylating agent. The team combined a range of aryl carbamates with triisopropylsilyl ether (TIPS)-protected propargyl alcohols using [RhCl(C2H4)2] as a catalyst, an N-heterocyclic carbene (NHC) as a ligand and K3PO4 as a base in toluene at 130 °C.

The reaction gives the desired aryl acetylenes (pictured) in good yields and tolerates functional groups such as ketones, esters, and amides. It proceeds via C−O bond activation at the carbamate, which acts as an ortho-directing group. According to the researchers, the synthesized functionalized aromatic alkynes can serve as useful building blocks in organic synthesis.


Article Views: 1435

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. more

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