Premium
A Novel Water‐Soluble m ‐TPPTC Ligand: Steric and Electronic Features –Recent Developments in Pd‐ and Rh‐Catalyzed CC Bond Formations
Author(s) -
Genin Emilie,
Amengual Rémi,
Michelet Véronique,
Savignac Monique,
Jutand Anny,
Neuville Luc,
Genêt JeanPierre
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404218
Subject(s) - chemistry , sonogashira coupling , steric effects , tppts , aryl , catalysis , ligand (biochemistry) , electronic effect , selectivity , copper , medicinal chemistry , palladium , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , rhodium , receptor , biochemistry , alkyl , hydroformylation
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 CC 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.