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697575

Sigma-Aldrich

(Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate

Synonym(s):

JohnPhos Au(MeCN)SbF6

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About This Item

Empirical Formula (Hill Notation):
C22H30AuF6NPSb
CAS Number:
866641-66-9
Molecular Weight:
772.17
MDL number:
MFCD11045449
UNSPSC Code:
12161600
PubChem Substance ID:
329761933
NACRES:
NA.22

form

solid

reaction suitability

core: gold
reagent type: catalyst

mp

198-203 °C (D)

SMILES string

[Au+].CC#N.F[Sb-](F)(F)(F)(F)F.CC(C)(C)P(c1ccccc1-c2ccccc2)C(C)(C)C

InChI

1S/C20H27P.C2H3N.Au.6FH.Sb/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16;1-2-3;;;;;;;;/h7-15H,1-6H3;1H3;;6*1H;/q;;+1;;;;;;;+5/p-6

InChI key

ADQOZROJMVWPRI-UHFFFAOYSA-H

General description

(Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate is a phosphine ligated gold(I) complex. It is used as a catalyst in a domino reaction to form C–C, C–N, and C–O bonds due to the ease with which it can activate C=C and C≡C bonds, thus allowing for unique rearrangements or reactions with various nucleophiles. Gold catalysis provides an excellent method to construct complex chemical architectures in a mild manner that would be difficult to achieve using other reaction paradigms.

Application

Gold Catalysts — 21st Century ′Gold Rush′

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 + H332,H411

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Echavarren Group – Professor Product Portal

The research of the Echavarren group centers on the development of new reactions based on the use of electrophilic complexes of Au(I), Pt(II), and other transition metals as catalysts and their applications in organic synthesis of complex, biologically active molecules. The Echavarren group is also examining new strategies for the synthesis of polyarenes of interest in material science. In particular, they are interested in the ready construction of C-60 skeletons using reactions catalyzed by Pd(0) and other transition metals.

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