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A new suzuki-heck-type coupling cascade: indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons
Hermann A Wegner1, Lawrence T Scott, Armin De Meijere
1Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany.
The Journal of Organic Chemistry
|February 1, 2003
Abstract:
Under palladium catalysis, o-bromobenzeneboronic acid can be coupled with 1-bromonaphthalene (6) and with oligocyclic bromoarenes to furnish indeno-annelated polycyclic aromatic hydrocarbons 1-4 and 25 in a single operation in moderate to good yields (27-87%). Alternatively, o-dibromoarenes and 1,2-dibromocycloalkenes can be cross-coupled with 1-naphthaleneboronic acid under the same conditions to yield analogous products (6-87%), and indenocorannulene (19) can be prepared likewise in a single step from pinacol corannuleneboronate (18) (40%).