the hydroarylation reaction—scope and limitations的hydroarylation reaction-scope和局限性.pdf

Molecules 2010, 15, 3402-3410; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review The Hydroarylation Reaction—Scope and Limitations 1 1 1 1 1 Jan C. Namyslo , Jörg Storsberg , Jens Klinge , Christian Gärtner , Min-Liang Yao , Nuket Ocal 2 and Dieter Eckhard Kaufmann 1,* 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; E-Mail: dieter.kaufmann@tu-clausthal.de; Tel.: +49-5323-70 2027; Fax: +49-5323-70 2834. Received: 25 February 2010; in revised form: 30 April 2010 / Accepted: 6 May 2010 / Published: 10 May 2010 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