One step entry to P,O- and P,N-type heterocyclic tertiary phosphine ligands and application in Suzuki-Miyaura cross-coupling reactions.

@article{Ullah2011OneSE,
  title={One step entry to P,O- and P,N-type heterocyclic tertiary phosphine ligands and application in Suzuki-Miyaura cross-coupling reactions.},
  author={Ehsan Ullah and James McNulty and Christine Kennedy and A. J. Robertson},
  journal={Organic \& biomolecular chemistry},
  year={2011},
  volume={9 12},
  pages={
          4421-4
        }
}
A direct synthesis of conformationally mobile P,O- and P,N-type heterocyclic phosphine ligands is described involving radical-mediated addition of diisobutylphosphine to olefinic-heterocycles. Palladium complexes of the P,N-ligand were determined to be highly active in the Suzuki-Miyaura cross-coupling reactions, including deactivated aryl chlorides. 
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References

SHOWING 1-10 OF 56 REFERENCES
A novel P,O-type phosphorinane ligand for the Suzuki–Miyaura cross-coupling of aryl chlorides
Abstract The Pd-mediated Suzuki–Miyaura cross-coupling of substituted and unsubstituted aryl chlorides with phosphorinane ligands was investigated uncovering an interesting ligand effect. The scopeExpand
A simple and highly efficient P,O-type ligand for Suzuki-Miyaura cross-coupling of aryl halides.
A simple and efficient hemilabile-type phosphine ligand, found to be highly effective in Suzuki-Miyaura cross-coupling of aryl chlorides with generally low Pd-catalyst loading (0.05%), was preparedExpand
Solid-phase Suzuki cross-coupling reactions using a phosphine ligand based on a phospha-adamantane framework
Abstract The use of a catalyst system based on Pd 2 dba 3 ·CHCl 3 and 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane allows for Suzuki coupling aryl halides with an array of boronicExpand
Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts.
TLDR
A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates and a challenging example for room temperature coupling is realized. Expand
Phosphorinanes as ligands for palladium-catalyzed cross-coupling chemistry.
TLDR
Phosphorinanes are presented as a class of phosphine ligand suitable for organopalladium cross-coupling chemistry and library screening and applications of these ligands in the Suzuki, Sonogashira, ketone arylation, and aryl amination reactions are presented. Expand
Spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline ligands for iridium-catalyzed enantioselective hydrogenation of ketimines.
From imines to amines through catalysis by Ir(I) complexes of a new type of P,N ligand (see scheme): This reaction affords the corresponding optically active amines with up to 98 % ee and has alsoExpand
Proline-based P, N ligands in asymmetric allylation and the Heck reaction.
TLDR
A series of phosphine-oxazoline ligands based on proline are reported, which gave a palladium complex, which catalyzed the addition of dimethylmalonate to cyclopentenyl acetate in excellent yield and up to 96% ee. Expand
PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis
Chiral phosphinooxazolines (PHOX ligands), which coordinate to a metal center with a N- and a P-atom, allow effective enantiocontrol in a variety of metal-catalyzed reactions. They are readilyExpand
Efficient palladium-catalysed carbonylative and Suzuki–Miyaura cross-coupling reactions with bis(di-tert-butylphosphino)-o-xylene
The use of the ligand bis(di-tert-butylphosphino)-o-xylene (dtbpx) in palladium-catalysed carbonylative and Suzuki–Miyaura cross-coupling reactions is described. Aryl and vinyl halides readilyExpand
Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst
A PdP(t-Bu)3 catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines couldExpand
...
1
2
3
4
5
...