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Synthesis and Functionalisation of 5-Substituted Neocuproine Derivatives

✍ Scribed by Jan P. W. Eggert; Ulrich Lüning; Christian Näther

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
155 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

2,9‐Dimethyl‐1,10‐phenanthroline (neocuproine, 1) was functionalised selectively in the 5‐position. Silylation of the methyl groups followed by bromination in the 5‐position was carried out to give the bis(tert‐butyldimethylsilyl)‐substituted neocuproine 3 and 5‐bromo‐2,9‐dimethyl‐1,10‐phenanthroline (4) after deprotection. Compounds 3 and 4 are versatile building blocks for the construction of 5‐substituted neocuproines. Palladium‐catalysed couplings (Suzuki, Sonogashira, Buchwald/Hartwig) can be utilized to connect different substituents to the 1,10‐phenanthroline moiety (5–7). These substituents may carry additional functional groups that allow the further connection of the 5‐substituted neocuproines to form other molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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