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Synthesis 2002(6): 0749-0752
DOI: 10.1055/s-2002-25769
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
Weitere Informationen
Publikationsverlauf
Received
11 December 2001
Publikationsdatum:
26. April 2002 (online)


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.
Key words
Stille coupling - 1,8-dipyridylnaphthalenes - 2,4-disubstituted pyridines - Ziegler reaction - atropisomers