Synthesis of dicarboxylate "C-clamp" 1,2-diethynylarene compounds as potential transition-metal ion hosts

Erwin Reisner, Stephen J. Lippard

    Research output: Contribution to journalArticlepeer-review

    Abstract

    We report an efficient convergent synthesis of a new type of C-clamp ligand with a 1,2-diethynylarene scaffold involving a chelate host capable of binding a guest molecule in its endo-dicarboxylate pocket. The chemistry involves a combination of palladium-catalyzed Sonogashira, Heck, and Suzuki cross-coupling reactions. The compounds 2,3-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl] triptycene and 4,5-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl]veratrole and their 2′-carboxy-m-terphenyl-4-yl analogues were designed as dinucleating ligands to assemble carboxylate-bridged transition-metal complexes with a windmill geometry. The X-ray crystal structure of one such C-clamp compound containing co-crystallized water molecules reveals strong hydrogen bonds of the aqua guest to the endo-oriented carboxylic acid entities of the C-clamp host. In addition, two syn-N-donor ligands were prepared as a synthetic scaffold to mimic the geometric arrangement of N-donor atoms in carboxylate-bridged dinuclear proteins. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
    Original languageEnglish
    Pages (from-to)156-163
    Number of pages7
    JournalEuropean Journal of Organic Chemistry
    Issue number1
    DOIs
    Publication statusPublished - 2008

    Keywords

    • Bridging ligands
    • C-C coupling
    • Carboxylate ligands
    • Chelates
    • Cross-coupling

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