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667412

Sigma-Aldrich

Pentamethylcyclopentadienyltris (acetonitrile)ruthenium(II) hexafluorophosphate

Synonym(s):

[RuCp*(MeCN)3]PF6

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About This Item

Empirical Formula (Hill Notation):
C16H24N3PRuF6
CAS Number:
Molecular Weight:
504.42
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

core: ruthenium
reagent type: catalyst

storage temp.

2-8°C

SMILES string

[Ru+].CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.CC1C(C)=C(C)C(C)=C1C

InChI

1S/C10H16.3C2H3N.F6P.Ru/c1-6-7(2)9(4)10(5)8(6)3;3*1-2-3;1-7(2,3,4,5)6;/h6H,1-5H3;3*1H3;;/q;;;;-1;+1

InChI key

IYEMDYLFXFMECZ-UHFFFAOYSA-N

General description

Pentamethylcyclopentadienyltris (acetonitrile)ruthenium(II) hexafluorophosphate is an organoruthenium compound. It is used as a homogeneous catalyst in organic synthesis. It enables the hydrosilylation of alkynes, cyclotrimerization of alkynes, cycloaddition reactions, and carbon-carbon or carbon-heteroatom bond-forming reactions.

Application

A versatile catalyst for hydrosilylation of alkynes providing α-vinylsilanes.
Reagent use as catalyst precursors for carbon-carbon or carbon-heteroatom bond forming reactions.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes.
B M Trost et al.
Journal of the American Chemical Society, 123(50), 12726-12727 (2001-12-14)
Barry M Trost et al.
Journal of the American Chemical Society, 127(50), 17644-17655 (2005-12-15)
The complex [Cp*Ru(MeCN)3]PF6 is shown to catalyze the hydrosilylation of a wide range of alkynes. Terminal alkynes afford access to alpha-vinylsilane products with good regioselectivity. Deuterium labeling studies indicate a clean trans addition process is at work. The same complex

Articles

Vinyl-metal reagents play a pivotal role in organic synthesis. Among the vinyl-metal reagents available, silicon-based reagents are of increasing importance. This is largely due to their low cost, minimal toxicity, ease of handling, and the simplicity of byproduct removal.

This robust protocol for hydrosilylation of terminal acetylenes to give α-vinylsilanes using [Cp*Ru(MeCN)3]PF6, as well as a number of other catalysts for hydrosilylation, comes from the Trost group at Stanford University.

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