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Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling Reactions

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Tilman Lechel†, Jyotirmayee Dash†‡, Paul Hommes†, Dieter Lentz† and Hans-Ulrich Reissig†

^† Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany

^‡ Indian Institute of Science, Education and Research Kolkata, Mohanpur Campus, Mohanpur 741252, Nadia, West Bengal, India

J. Org. Chem., 2010, 75 (3), pp 726–732

DOI: 10.1021/jo9022183

Publication Date (Web): December 23, 2009

hans.reissig@chemie.fu-berlin.de

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

A three-component reaction with lithiated alkoxyallenes, nitriles, and perfluorinated carboxylic acids as precursors led to a series of perfluoroalkyl- or perfluoroaryl-substituted 4-hydroxypyridine derivatives. These compounds were converted into 4-pyridyl nonaflates which can be employed as versatile building blocks for the synthesis of π-conjugated compounds with use of palladium-catalyzed couplings. Suzuki reactions at C-4 and C-3 of the pyridine ring proceeded with moderate to high yields. In addition, Suzuki−Miyaura, Stille, or Buchwald−Hartwig coupling reactions have also been studied and afforded the corresponding highly substituted pyridine derivatives. Starting from an arylated propargylic ether the three-component reaction led to a pentasubstituted 4-hydroxypyridine derivative that could also be employed in palladium-catalyzed processes at C-4 and at C-3 of the pyridine core. With this simple approach the sterically highly crowded 3,4,5-triphenyl-substituted pyridine derivative 37a could be prepared and studied by an X-ray analysis. With acetonitrile as precursor a different reaction pathway was found when this component was used in excess resulting in a pyridine derivative with a new substitution pattern. In summary, the methods described here allow a flexible and fairly efficient entry to a variety of highly substituted pyridine derivatives bearing perfluorinated alkyl or aryl groups.

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