Alkylation of Amides under Mild Conditions

  • Author:
  • Published: 13 May 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Alkylation of Amides under Mild Conditions

Transition-metal-catalyzed cross-coupling reactions are very useful tools in organic synthesis. However, they often require expensive metals such as palladium. Nickel is a good alternative with a lower cost and good catalytic activity.

Magnus Rueping, RWTH Aachen University, Germany, and King Abdullah University of Science and Technology (KAUST), Thuwal, Saudi Arabia, and colleagues have developed a nickel-catalyzed cross-coupling of amides with alkylboranes under mild conditions. The team combined a range of N-arylated amides with a variety of B-alkyl-9-BBNs (pictured right, 9-BBN = 9-borabicyclo[3.3.1]nonane) using Ni(cod)2 (cod = 1,5-cyclooctadiene) as a catalyst, an N-heterocyclic carbene (NHC) as a ligand, K2CO3 as a base, and LiCl as an additive. The reactions were performed in diisopropyl ether at 90 °C.

The desired products were obtained in good to high yields. The reaction tolerates a range of functional groups both at the amide and at the alkylborane, even carboxylic acid-derived groups such as esters.


Article Views: 1279

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, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH