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Molecules 2010, 15(5), 3402-3410; doi:10.3390/molecules15053402

The Hydroarylation Reaction—Scope and Limitations

1
Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany
2
Department of Chemistry, Faculty of Arts and Sciences, Davutpasa Campus, Yildiz Technical University, 34210 Esenler-Istanbul, Turkey
*
Author to whom correspondence should be addressed.
Received: 25 February 2010 / Revised: 30 April 2010 / Accepted: 6 May 2010 / Published: 10 May 2010
(This article belongs to the Special Issue Heck Coupling)
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Abstract

The synthetic potential of stereoselective, palladium-catalyzed hydro(het)arylation reactions of bi-, tri- and tetracyclic (hetero)alkenes 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-[2.2.1]heptenes 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 bicyclo[2.2.2]octenes react slower in hydroarylation reactions than the corresponding bicyclo[2.2.1]heptenes. The more flexible bicyclo[4.2.2]decene 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
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Namyslo, J.C.; Storsberg, J.; Klinge, J.; Gärtner, C.; Yao, M.-L.; Ocal, N.; Kaufmann, D.E. The Hydroarylation Reaction—Scope and Limitations. Molecules 2010, 15, 3402-3410.

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