Alkylation of Amides under Mild Conditions

  • Author: ChemistryViews.org
  • 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.


 

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