Synthesis and Functionalisation of 5‐Substituted Neocuproine Derivatives | Zendy

Eggert Jan P. W. | Zendy; Lüning Ulrich | Zendy; Näther Christian | Zendy

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Synthesis and Functionalisation of 5‐Substituted Neocuproine Derivatives

Author(s) -

Eggert Jan P. W.,

Lüning Ulrich,

Näther Christian

Publication year - 2005

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.200400635

Subject(s) - chemistry , moiety , sonogashira coupling , phenanthroline , halogenation , palladium , silylation , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis

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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