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Diphenyl-2-pyridylphosphine

Diphenyl-2-pyridylphosphine Acute toxicity (oral, dermal, inhalation), category 4 Skin irritation, category 2 Eye irritation, category 2 Skin sensitization, category 1 Specific Target Organ Toxicity – Single exposure, category 3

Diphenyl-2-pyridylphosphine is an organophosphorus compound with the formula P(C6H5)2(2-C5H4N). It is the most widely used mono-pyridylphosphine ligand. Other mono-pyridylphosphines ligands (3-, 4-) are not common in chemical literature; however, tris-pyridylphosphines have been thoroughly investigated as ligands in transition metal complexes used for catalysis.7 reference not specified -- Pyridylphosphines, including diphenyl-2-pyridylphosphine, may bind transition metals as monodentate or bidentate ligands4. Diphenyl-2-pyridylphosphine behaves as a P-bound monodentate ligand,3 reference not specified -- or a P,N-bound bidentate ligand. Diphenyl-2-pyridylphosphine is a sought after ligand for its ability to relay protons to transition metals such as palladium(II) in homogeneous catalysis.

Synthesis

Diphenyl-2-pyridylphosphine is prepared from 2-lithiopyridine with chlorodiphenylphosphine:

Diphenyl-2-pyridylphosphine is an integral ligand in the Pd(II) catalyzed carbonylation of alkynes. The pi-donor ability of one bidentate P,N-coordinated ligand is highly stabilizing to the metal center. While a second monodentate, N-protonated ligand transfers protons to the metal to be used in catalysis. The role of the pyridyl group in this catalytic cycle is evident when the ligand is replaced by triphenyl phosphine, and rates of catalysis a greatly decreased.3 reference not specified -- This catalytic process is an important step in the production of polymers, and other fine chemicals.

RC2H + CO + XH + Pd cat → RCCH2COX + RCHCHCOX Pd cat = Pd(OAc)2/Ph2PPy/ CH3SO3H R=alkyl, aryl X=OH, OR’, NR2’ Scheme 1: Carbonylation of alkynes by cationic Pd(II) catalyst with a diphenyl-2-pyridylphosphine ligand.6 reference not specified --

References

References

  1. (2007). "Improved synthesis of monodentate and bidentate 2- and 3-pyridylphosphines". Tetrahedron Letters.
  2. (1994). "Homogeneous catalysis by cationic palladium complexes. Precision catalysis in the carbonylation of alkynes". Journal of Organometallic Chemistry.
  3. (2009). "Investigation of the Dynamic Solution Behavior of Chloro(diene)rhodium(I) Phosphine Complexes with a Pendant Unsaturated Heterocycle at Phosphorus (2-pyridyl, 2-imidazyl; diene = COD, NBD)". Organometallics.
  4. (2006). "The first insoluble polymer-bound palladium complexes of 2-pyridyldiphenylphosphine: Highly efficient catalysts for the alkoxycarbonylation of terminal alkynes". Chem. Commun..
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tertiary-phosphines 2-pyridyl-compounds phenyl-compounds
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