Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles

…, N Rackelmann, MO Turcotte-Savard…

Index: Rudolph, Alena; Rackelmann, Nils; Turcotte-Savard, Marc-Olivier; Lautens, Mark Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 289 - 297

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Citation Number: 38

Abstract

A palladium-catalyzed, norbornene-mediated ortho-alkylation reaction of aryl iodides with secondary alkyl halides is described. Intermolecular or intramolecular ortho-alkylation proceeds in a domino process with various termination steps, generating two new carbon− carbon or carbon− nitrogen bonds in one pot, to afford an array of polycyclic heterocycles. The use of enantioenriched substrates has shown that this palladium-catalyzed reaction is ...