Synthesis 2002(6): 0749-0752
DOI: 10.1055/s-2002-25769
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Atropisomeric 1,8-Bis(4′,4′-dipyridyl)naphthalenes from 4-Trimethylstannylpyridines

Christian Wolf*, Bereket T. Ghebremariam
Department of Chemistry, Georgetown University, Washington, DC 20057, USA
Fax: +1(202)6876209; e-Mail: cw27@georgetown.edu;
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Publikationsverlauf

Received 11 December 2001
Publikationsdatum:
26. April 2002 (online)

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Abstract

Two synthetic strategies towards atropisomeric 2′,2′-di­substituted 1,8-bis(4′,4′-dipyridyl)naphthalenes using Stille cross-coupling of trimethylstannylpyridine derivatives and 1,8-di­iodonaphthalene have been investigated. Introduction of substituents into the pyridyl moieties prior to the cross-coupling step provides higher overall yields than derivatization of 1,8-bis(4′,4′-dipyridyl)naphthalene under Ziegler reaction conditions.