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ω‐Alkyne‐Mono‐ and Diphosphonates – Synthesis and Sonogashira Cross‐Coupling Reaction with Aryl Halides
Author(s) -
DelainBioton Lise,
Villemin Didier,
Jaffrès PaulAlain
Publication year - 2007
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.200600556
Subject(s) - alkyne , chemistry , sonogashira coupling , phosphonate , aryl , linker , alkyl , halide , combinatorial chemistry , ether , ligand (biochemistry) , organic chemistry , polymer chemistry , palladium , catalysis , biochemistry , receptor , computer science , operating system
A convergent approach to functionalise aromatic compounds with a linker terminated by a phosphonate group is reported. The starting point of this strategy is the synthesis of five new ω‐alkyne‐phosphonates. The linker between the phosphonate group and the alkyne part is either an alkyl or an ether chain. This strategy is based on the use of the phosphonate group as the anchoring point for the attachment of organic compounds onto alumina and the alkyne group, which is used to functionalise aryl halide compounds by a Sonogashira cross‐coupling. The use of 1,10‐phenanthroline as substrate illustrates the application of this strategy to an aromatic ligand. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)