Tetrakis(triphenylphosphine)palladium(0)

• Catalog No.: 10548
• CAS Number: 14221-01-3
• M. F.: C72H60P4Pd
• M. W.: 1155.561844
• Purity: 99.8% (metals basis), Pd 9% min

SYNONYMS

• Title: 四(三苯基膦)钯
• IUPAC name: tetrakis(triphenylphosphane) palladium
• IUPAC Traditional name: tetrakis(triphenylphosphine) palladium
• Synonyms: Palladium(0) tetrakis(triphenylphosphine)

DATABASE IDS

• CAS Number: 14221-01-3
• Beilstein Number: 6704828
• MDL Number: MFCD00010012
• EC Number: 238-086-9

PROPERTIES

• Purity: 99.8% (metals basis), Pd 9% min
• Apperance: Crystalline
• Melting Point: 100-105°C
• Solubility: Soluble in benzene, ethanol and chloroform
• GHS Hazard statements: H413
• GHS Precautionary statements: P273-P501A
• Risk Statements: 53
• Safety Statements: 60-61
• Storage Warning: Air Sensitive
• TSCA Listed: 是

REFERENCES

• The conversion of aryl halides or triflates to benzonitriles can be much improved by the use of the catalyst in combination with Zn(CN)₂ in DMF or NaCN/CuI (cat) in acetonitrile, giving good yields at lower temperatures than the classical Rosenmund-von Braun method (see Copper(I) cyanide, 12135): Tetrahedron Lett., 39, 2907 (1998); J. Org. Chem., 63, 8224 (1998). Vinyl bromides or iodides with KCN/18-crown-6 give acrylonitriles in high yield with retention of configuration: Tetrahedron Lett., 4429 (1977). Vinyl triflates with LiCN can also be used: J. Chem. Soc., Chem. Commun., 756 (1989). For a review of palladium- and copper-catalyzed cyanation reactions, see: Eur. J. Inorg. Chem., 3513 (2004).
• Allylic esters, halides, etc. form organopalladium intermediates equivalent to allyl cations and react with various nucleophiles, e.g. amines: J. Am. Chem. Soc., 98, 8516 (1976); J. Org. Chem., 44, 3451 (1979); Tetrahedron Lett., 24, 2745 (1983); Org. Synth. Coll., 8, 13 (1993). For stereoselective introduction of an amino group using sodium azide, see: J. Org. Chem., 54, 3292 (1989).
• Catalyst for a variety of carbonylation reactions. Aryl, vinyl, benzylic and allylic halides with CO (1-3 atm) in the presence of Bu₃SnH give aldehydes: J. Am. Chem. Soc., 105, 7175 (1983); 108, 452 (1986). For carbonylative intramolecular cyclization of aminomethyl vinyl triflates to ɑ?-unsaturated lactams, see: Tetrahedron, 51, 5585 (1995):
  
• Acyl halides can be coupled with organometallic reagents to give ketones, e.g. organozinc halides: Tetrahedron Lett., 24, 5181 (1983); Org. Synth. Coll., 8, 274 (1993), organotin reagents: Org. Synth. Coll., 8, 268 (1993), or arylboronic acids: Tetrahedron Lett., 40, 3109 (1999).
• Homogeneous catalyst for a wide variety of organometallic coupling reactions.
• Numerous methods have been developed for the synthesis of unsymmetrical biaryls, many of which are catalyzed by this Pd(0) complex. Aryl halides or triflates can be coupled with, e.g. Grignard reagents: Tetrahedron, 42, 2111 (1986), arylzinc halides: Org. Synth. Coll., 8, 430 (1993), organotin reagents (Stille): Angew. Chem. Int. Ed., 25, 508 (1986); J. Am. Chem. Soc., 109, 5478 (1987), or boronic acids (Suzuki-Miyaura): Synth. Commun., 11, 513 (1981); Chem. Rev., 95, 257 (1995); see Benzeneboronic acid, A14257, and Appendix 5.
• Vinyl iodides couple stereoselectively with alkyl, aryl or vinyl Grignards: Tetrahedron Lett., 191 (1978). For stereoselective arylation of a vinylic bromide with an arylzinc chloride in a synthesis of the anti-estrogen agent (Z)-tamoxifen and derivatives, see: J. Org. Chem., 55, 6184 (1990):
  
• For an example of the coupling of a terminal acetylene with a vinyl bromide by the Sonogashira method using Copper(I) iodide, 11606, see: Org. Synth. Coll., 9, 117 (1998).