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CataCXium® Ligands and Catalysts for C-X Coupling Reactions

Phosphines with excellent activities in various Pd (but not only)-catalyzed coupling reactions

Solvias cataCXium ligands represent highly effective phosphines that became an essential constituent part of Palladium-catalyzed coupling processes. Very often organic transformations such as Suzuki reactions, Sonogashira couplings or Buchwald-Hartwig reactions make high demands on the employed catalyst.

The application of cataCXium catalytic systems usually based on palladium complexes with bulky, electron-rich ligands, enables significant advances in substrate scope under mild conditions with low catalyst loadings. They are stable for a period of at least 3 months in air at room temperatures in a solid state, however very unstable in air in solution.

cataCXium® C (46-0290), also known as Herrmann-Beller’s catalyst [1], is one of the best catalysts used for Heck reactions. This palladacycle complex is an air-stable material that is highly soluble in dichloromethane, medium soluble in THF and toluene. cataCXium® C is able to reach high catalyst turnover numbers with minimum catalyst loadings [2-3].


Fig. 1. CataCXium® C – Herrmann-Beller’s catalyst

CataCXium® A includes a phosphine ligand consisting of adamantyl groups. CataCXium® A (15-0483) cataCXium® ABn (15-0038), cataCXium® AHI (15-0495) are show high activities in Suzuki [4] and Heck couplings [5], but also in Pd-catalyzed amination [5], arylation [6] and formylation of aryl bromides [7]. Also, CataCXium® A is used in Ni(0) catalyzed denitrogenative alkyne insertion reactions [8].

Fluorenederived ligand group CataCXium® F involves cataCXium® FBn (15-1072), cataCXium® FBu (15-1074), cataCXium® FPrPh (15-1076) and cataCXium® FSulf (15-1072). These 9-fluorenylphosphines were shown to be high activity catalysts in the Pd-Catalyzed Sonogashira, Suzuki, and Buchwald-Hartwig coupling reactions, not only in organic solvents but also in water [9-10].

Under the trade name CataCXium® P, products are based on pyrrole (15-2975, 15-2980, 15-3600, 15-3610), indol (15-3550, 15-3605), and imidazole (15-6362) scaffolds. These ligands form efficient catalytic systems that show outstanding catalytic performance with a Pd-promoted process [11]. For example, cataCXium® PCy (15-3610) is an excellent ligand for general synthesis of Ru-catalyzed primary amines by amination of secondary alcohols with ammonia [12]. For more details, please review corresponding technical notes.



  1.  Angew. Chem. Int. Ed. 1995, 17, 1844.
  2.  Org. Lett., 2003, 5, 3285.
  3.  Catalysts 2020, 10, 989.
  4.  Angew. Chem. Int. Ed., 2000, 39, 4153.
  5.  Synlett, 2000, 1589.
  6.  J. Mol. Catal. A: Chem., 2002, 515, 182.
  7.  Angew. Chem., Int. Ed., 2006, 45, 154.
  8.  Chem. Commun., 2009, 1470.
  9.  Chem. Eur. J. 2007, 13, 2701.
  10.  A Europ. J. 2008, 14, 4267.
  11.  ChemSusChem 2008, 1, 91.
  12.  Angew. Chem. Int. Ed. 2010, 49, 8126.



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