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254037 Sigma-Aldrich

Chloro(triphenylphosphine)gold(I)

≥99.9% trace metals basis

Synonym: (Ph3P)AuCl, Triphenylphosphinegold(I) chloride

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Gold Catalysts, Gold Complexes
Quality Level   100
assay   ≥99.9% trace metals basis
reaction suitability   reagent type: catalyst
SMILES string   Cl[Au].c1ccc(cc1)P(c2ccccc2)c3ccccc3
InChI   1S/C18H15P.Au.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h1-15H;;1H/q;+1;/p-1
InChI key   IFPWCRBNZXUWGC-UHFFFAOYSA-M

Description

Application

Gold Catalysts — 21st Century ′Gold Rush′

Catalyst employed in the cyclization of O-propargyl carbamates to alkylideneoxazolidinones via a 5-exo-digonal pathway at room temperature. Also catalyzes the cycloisomerization of enynes containing a cyclic olefin into highly-fused, polycyclic dienes at room temperature.

Reagent is used with cocatalytic halide abstraction agent to activate π-systems toward addition by heteroatom and carbon nucleophiles.

Packaging

5 g in poly bottle

500 mg in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Catalysts
Protocols & Articles

Articles

Fluorinating Reagents

The importance of selectively fluorinating compounds in medicinal chemistry, biology, and organic synthesis is well appreciated and provides a major impetus to the discovery of new and mild fluorinat...
Aldrich ChemFiles 2006, 6.2, 5.
Keywords: Fluorinations, Medicinal chemistry, Metathesis, Organic synthesis

Gold Catalysis - Aldrich ChemFiles 2007, 7.5, 10.

Gold catalysis is playing an increasing role in organic synthesis for the facile construction of complex architectures not readily accessed by standard methods. Gold catalysts mediate unique C–C, C–O...
Aldrich ChemFiles 2007, 7.5, 10.
Keywords: Catalysis, Chemfiles, Enyne rearrangements, Heterocycle formation, Isomerizations, Methods, Organic synthesis, Rearrangements

Intramolecular Hydroamination

An example of the potency of gold catalysis in hydroamination reactions was highlighted in 2006 by Crawley and Funk in the multistep synthesis of communesin B.1 One of the key steps in the synthesis ...
William Sommer
Aldrich ChemFiles 2009, 9.5, 3.
Keywords: Catalysis, Chemfiles, Hydroaminations

Related Content

Gold Catalyst in Chemical Synthesis

Introduction Hashmi, Toste, Echavarren, and Haruta, among others, have fueled the advance of gold into the forefront of transition metal catalysis.1,2 Phosphine ligated gold(I) complexes have risen a...
Keywords: Asymmetric synthesis, Building blocks, Catalysis, Claisen rearrangement, Conia-Ene Reaction, Cyclizations, Cycloadditions, Cycloisomerizations, Cyclopropanations, Deprotonations, Ene reaction, Hydroaminations, Hydrogenations, Isomerizations, Ligands, Rautenstrauch rearrangements, Rearrangements, Reductions, Schmidt Reaction, Substitutions

Peer-Reviewed Papers
15

References

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