Herrmann's catalyst

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Herrmann's catalyst
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 681-425-4
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/2C21H20P.2C2H4O2.2Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;2*1-2(3)4;;/h2*4-15H,1H2,2-3H3;2*1H3,(H,3,4);;/q2*-1;;;2*+2/p-2
    Key: AQTSNKXEMWZOGA-UHFFFAOYSA-L
  • CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)[O-].CC(=O)[O-].[Pd+2].[Pd+2]
Properties
C46H46O4P2Pd2
Molar mass 937.66 g·mol−1
Appearance Yellow solid
Melting point 123–125 °C (253–257 °F; 396–398 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Herrmann's catalyst is an organopalladium compound that is a popular catalyst for the Heck reaction. It is a yellow air-stable solid that is soluble in organic solvents. Under conditions for catalysis, the acetate group is lost and the Pd-C bond undergoes protonolysis, giving rise to a source of "PdP(o-tol)3".

The complex is made by reaction of tris(o-tolyl)phosphine with palladium(II) acetate:[1]

2 Pd(OAc)2 + 2 P(o−tolyl)3 → 2 HOAc + Pd2(OAc)2[P(o−tolyl)(o−tolyl)2]2

Many analogues of Hermann's catalyst have been developed, e.g. palladacycles obtained from 2-aminobiphenyl.[2]

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Retrieved from "http://70.231.62.181/index.php?title=Herrmann%27s_catalyst&oldid=19182606"