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Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides:  An Efficient System Even in an Air Atmosphere

Organic Letters · 2002 · Vol. 4(4) · pp. 581–584
Fuk Yee KwongArtis KlaparsStephen L. Buchwald

Abstract

[reaction: see text] A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atmosphere with comparable yield. Preliminary results on the amination of aryl bromides are also described.

Catalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAminationChemistryArylCatalysisYield (engineering)CopperEthylene glycolOrganic chemistryCombinatorial chemistryCoupling reaction

MeSH terms

AminationAminesCatalysisCopperEthylene GlycolsIodides

Funding

  • Pfizer
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