Sterically Demanding, Zwitterionic Trialkylphosphonium Sulfonates as Air-Stable Ligand Precursors for Efficient Palladium-Catalyzed Cross-Couplings of Aryl Bromides and Chlorides

Abstract 3-(Di-TERT-butylphosphonium)propane sulfonate (DTBPPS) and 3-(diadamantylphosphonium)propane sulfonate (DAPPS) are air-stable pre-ligands for aqueous-phase palladium-catalyzed cross-coupling reactions. Both DTBPPS and DAPPS were found to give active catalysts for the Sonogashira coupling of...

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Published in:Synthesis (Stuttgart) 2008-06, Vol.2008 (12), p.1965-1970
Main Authors: Brown, William S., Boykin, D’Ariel D., Sonnier, M. Quentin, Clark, William D., Brown, Fallon V., Shaughnessy, Kevin H.
Format: Article
Language:English
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Summary:Abstract 3-(Di-TERT-butylphosphonium)propane sulfonate (DTBPPS) and 3-(diadamantylphosphonium)propane sulfonate (DAPPS) are air-stable pre-ligands for aqueous-phase palladium-catalyzed cross-coupling reactions. Both DTBPPS and DAPPS were found to give active catalysts for the Sonogashira coupling of aryl bromides at room temperature and 4-chloroanisole at 80 °C. These ligands also gave effective catalysts for the aqueous-phase Suzuki coupling of aryl bromides at room temperature.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2008-1067095