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Synthesis 1998; 1998(2): 148-152
DOI: 10.1055/s-1998-2013
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Palladium-Catalyzed Coupling Reactions of 1-Bromoadamantane with Styrenes and Arenes

Stefan Bräse* , Bernard Waegell, Armin de Meijere
  • *Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany; Fax + 49(5 51)39 94 75; E-mail: ameijer1@uni-goettingen.de
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Publication History

Publication Date:
31 December 2000 (online)

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The palladium-catalyzed reaction of 1-bromoadamantane (1-Br) with styrene and donor-substituted styrenes gave the corresponding Heck-type coupling products 3 a and b, and 5 a and b in moderate yields (15-41%), while the reaction of 1-Br with various arenes 6 a - p under palladium catalysis gave the corresponding adamantyl-substituted arenes 7 a - p in good to excellent yields (35-98%).

cross-coupling reactions - metal-catalyzed/adamantylation of styrene and alkenes/arylation of 1-bromoadamantane/Heck reaction - palladium catalysis