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Palladium‐Catalyzed Synthesis of Nonsymmetrically Functionalized Bipyridines, Poly(bipyridines) and Terpyridines
Author(s) -
Puglisi Alessandra,
Benaglia Maurizio,
Roncan Giulia
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390214
Subject(s) - stille reaction , chemistry , palladium , combinatorial chemistry , pyridine , suzuki reaction , supramolecular chemistry , aldehyde , coupling reaction , catalysis , polymer chemistry , organic chemistry , molecule
Abstract Palladium‐catalyzed coupling reactions were employed to prepare nonsymmetric, densely functionalized bipyridines and oligo(bipyridines), featuring sensitive functionalities like alcohol, ester and aldehyde groups. Stille coupling between halo(poly)pyridine and the proper (poly)pyridyltin derivative afforded in good yields nonsymmetric, derivatized oligo(bipyridines), amenable to further synthetic modifications. The methodology was used also to synthesize highly functionalized terpyridines. A series of Suzuki and Stille palladium‐promoted coupling reactions allowed us to obtain in good yields terpyridines bearing two different and differently functionalizable groups, valuable building blocks for the construction of complex supramolecular frameworks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)