The Hydroarylation Reaction—Scope and LimitationsReportar como inadecuado

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Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany


Department of Chemistry, Faculty of Arts and Sciences, Davutpasa Campus, Yildiz Technical University, 34210 Esenler-Istanbul, Turkey


Author to whom correspondence should be addressed.

Abstract The synthetic potential of stereoselective, palladium-catalyzed hydrohetarylation reactions of bi-, tri- and tetracyclic heteroalkenes in the presence of phospines and arsines as highly efficient ligands was studied. The mechanism of this reductive Heck reaction becomes more complex in the case of benzonorbornenes. Hydroarylation of diazabicyclo-2.2.1heptenes provides a stereoselective access to aryldiaminocyclopentanes. Electron-deficient arylpalladium complexes shift the reaction towards the product of a formal 1,2-hydrazidoarylation reaction of 1,3-cyclopentadiene by a stereoselective C-N cleavage. Due to steric reasons, rigid bicyclo2.2.2octenes react slower in hydroarylation reactions than the corresponding bicyclo2.2.1heptenes. The more flexible bicyclo4.2.2decene system already tends to undergo domino-Heck reactions, even under reductive conditions. When a tetracyclic cis-allylcyclopropane is carbopalladated in the presence of formates, the neighboring cyclopropane ring is attacked in the first reported example of a π,σ domino-Heck reaction.

Keywords: homogenous catalysis; palladium; C-C coupling; domino reaction; rearrangement; mechanism homogenous catalysis; palladium; C-C coupling; domino reaction; rearrangement; mechanism

Autor: Jan C. Namyslo 1, Jörg Storsberg 1, Jens Klinge 1, Christian Gärtner 1, Min-Liang Yao 1, Nuket Ocal 2 and Dieter Eckhard Kaufmann 1,*



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