Substance
ID:739278
Names and Identifiers
IUPAC name
tetrakis(triphenylphosphane) palladium
IUPAC Traditional name
tetrakis(triphenylphosphine) palladium
Synonyms
Tetrakis(triphenylphosphine)palladium(0)Palladium(0) tetrakis(triphenylphosphine)四(三苯基膦)钯
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Properties
Safety Information
GHS Hazard statements
H413
TSCA Listed
是
GHS Precautionary statements
P273-P501A
Risk Statements
53
Safety Statements
60-61
Storage Warning
Air Sensitive
Physical Property
Melting Point
100-105°C
Apperance
Crystalline
Solubility
Soluble in benzene, ethanol and chloroform
Product Information
Purity
99.8% (metals basis), Pd 9% min
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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):
• 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):
• 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.
• 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).
• 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).
• 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).