4.4 Article

Iterative and regioselective cross-couplings of 2-chloro-3,4-diiodopyridine leading to 2,3,4-triheteroarylpyridines

Journal

TETRAHEDRON
Volume 66, Issue 3, Pages 668-675

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.066

Keywords

Palladium catalysis; Cross-coupling; Halogen dance; Suzuki-Miyaura reaction; Arylation; Arylpyridine; 2-Chloro-3,4-diiodopyridine

Funding

  1. EPSRC

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A one-pot synthesis of 2-chloro-3,4-diiodopyridine from 2-chloropyridine is described via a Directed ortho Metallation (DoM)/Halogen Dance (HD) mechanism in 26-28% yields. By performing sequential, iterative Suzuki-Miyaura cross-couplings using a variety of functionalised heteroaryl and arylboronic acids, a series of novel 2,3,4-triheteroarylpyridine scaffolds have been accessed in synthetically viable yields, including sterically hindered derivatives. 2-Chloro-4-heteroaryl-3-iodopyridines and 2-chloro-3,4-diheteroarylpyridines are also reported. The synthesis of 5-[3,4-bis(2-phenylethynyl)pyridin-2-yl]-2-fluoropyridine via a two-step Sonogashira/Suzuki-Miyaura reaction sequence from 2-chloro-3,4-diiodopyridine, phenylacetylene and 6-fluoropyridin-3-yl-3-boronic acid has been achieved in 48% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

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