ChemInform Abstract: Iterative and Regioselective Cross-Couplings of 2-Chloro-3,4-diiodopyridine Leading to 2,3,4-Triheteroarylpyridines

Autor:	Martin R. Bryce, Jamie S. Siddle, Adrian L. Ankers, Laura M. Daykin, Andrei S. Batsanov
Rok vydání:	2010
Předmět:	Steric effects chemistry.chemical_compound Reaction sequence Phenylacetylene Stereochemistry Chemistry Yield (chemistry) Halogen Regioselectivity Sonogashira coupling General Medicine Combinatorial chemistry
Zdroj:	ChemInform. 41
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.201022122
Popis:	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.
Databáze:	OpenAIRE
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