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Synlett 2001; 2001(Special Issue): 0920-0922
DOI: 10.1055/s-2001-14666
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The Dichotomy Between Benzene and Fulvene Formation in Palladium-Catalyzed Domino Tricyclizations of 2-Bromotetradec-1-ene-7,13-diynes

Stefan Schweizer* , Michael Schelper, Claudia Thies, Philip J. Parsons, Mathias Noltemeyer, Armin de Meijere
  • *Institut für Organische und Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2-4, 37077 Göttingen, Germany; Fax + 49 (551) 39-9475; E-mail: Armin.deMeijere@chemie.uni-goettingen.de
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Publication Date:
31 December 2001 (online)

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2-Bromotetradec-1-ene-7,13-diynes 1, 5, 12 with different substituents at the acetylenic terminus under palladium catalysis have been found to either yield an angularly bisannelated benzene derivative 3 (79%), or fulvene derivatives of type 5 (52-74%) as well as monoannelated fulvenes 13 b - e (32-48%). The mechanisms for all three reaction modes most probably involve intramolecular 5-exo-trig carbopalladations of an intermediate 1,3,5-hexatrienyl-6-palladium bromide intermediate.

palladium catalysis - cross coupling - cascade cyclizations - fulvenes