Palladium-mediated N-arylation of heterocyclic diamines: Insights into the origin of an unusual chemoselectivity

N Cabello-Sanchez, L Jean, J Maddaluno…

Index: Cabello-Sanchez, Noemi; Jean, Ludovic; Maddaluno, Jacques; Lasne, Marie-Claire; Rouden, Jacques Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 2030 - 2039

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Citation Number: 22

Abstract

The chemoselectivity of the palladium-mediated reaction of bromobenzene with various heterocyclic diamines was studied. Whatever the ligand used, 3-aminopyrrolidine underwent arylation of the secondary amine function (> 82%), whereas the more flexible 3- aminoazepinine was arylated on its primary function (> 70%). The ratio “arylation of primary amine versus arylation of secondary amine” of 3-aminopiperidine with bromobenzene ...