A Novel Water-Soluble m-TPPTC Ligand: Steric and Electronic Features -Recent Developments in Pd- and Rh-Catalyzed CC Bond Formations

The steric and electronic features of the novel water‐soluble phosphane m‐TPPTC have been determined using NMR, IR and UV‐VIS spectroscopic methods and compared to the well‐known sulfonated analogue TPPTS. The higher basicity of m‐TPPTC compared to TPPTS had an influence (selectivity and efficiency)...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2004-12, Vol.346 (13-15), p.1733-1741
Main Authors: Genin, Emilie, Amengual, Rémi, Michelet, Véronique, Savignac, Monique, Jutand, Anny, Neuville, Luc, Genêt, Jean-Pierre
Format: Article
Language:English
Subjects:
Alkynes
Analogue
Aromatic compounds
Basicity
Bonding
Electronics
Iodides
Palladium
phosphane basicity
recycling
rhodium
Sonogashira cross-couplings
water-soluble ligand
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Summary:The steric and electronic features of the novel water‐soluble phosphane m‐TPPTC have been determined using NMR, IR and UV‐VIS spectroscopic methods and compared to the well‐known sulfonated analogue TPPTS. The higher basicity of m‐TPPTC compared to TPPTS had an influence (selectivity and efficiency) either on Pd‐ or Rh‐catalyzed CC bond formations reactions. The Sonogashira copper‐free cross‐couplings of aryl iodides and ortho‐functionalized aryl iodides were efficiently performed using the carboxylated phosphane m‐TPPTC leading to the alkynes in high yields. The Pd/m‐TPPTC system was found to be efficiently recycled under mild biphasic conditions in the Sonogashira reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404218