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794139

Sigma-Aldrich

(η5 -Cyclopentadienyl)[N,N-dimethyl-Ν′-(2-pyridinylmethylidene)propane-1,3-diamine]ruthenium hexafluorophosphate

Synonym(s):

Herzon Reductive Hydration Catalyst

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About This Item

Empirical Formula (Hill Notation):
C16H22F6N3PRu
CAS Number:
1603164-23-3
Molecular Weight:
502.40
UNSPSC Code:
12161600
PubChem Substance ID:
329768426
NACRES:
NA.22

form

powder

Quality Level

100

reaction suitability

core: ruthenium
reagent type: catalyst

mp

>180 °C

SMILES string

CN(C)CCC/N=C/C1=NC=CC=C1.F[P-](F)(F)(F)(F)F.[C]2[C][C][C][C]2.[Ru+]

InChI

1S/C11H17N3.C5H5.F6P.Ru/c1-14(2)9-5-7-12-10-11-6-3-4-8-13-11;1-2-4-5-3-1;1-7(2,3,4,5)6;/h3-4,6,8,10H,5,7,9H2,1-2H3;1-5H;;/q;;-1;+1/b12-10+;;;

InChI key

KUSUXOOKLDLSSI-AKMNYRKMSA-N

Related Categories

General description

(η5 -Cyclopentadienyl)[N,N-dimethyl-N′-(2-pyridinylmethylidene)propane-1,3-diamine]ruthenium hexafluorophosphate is also referred to as Herzon reductive hydration catalyst. Herzon reductive hydration catalyst is a half-sandwich ruthenium complex. It is a tridentate nitrogen-based ligand containing a hemilabile 3-(dimethylamino)propyl group. It participates in the conversion of terminal alkynes to linear alcohols.

Application

Catalyst mediates the transformation of alkynes to alcohols through an anti-Markovnikov addition. This reaction occurs at room temperature with the use of formic acid to assist in the reduction of the intermediate aldehyde to the corresponding alcohol.

Other Notes

A Highly Active and Air-Stable Ruthenium Complex for the Ambient Temperature Anti-Markovnikov Reductive Hydration of Terminal Alkynes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Mingshuo Zeng et al.
Journal of the American Chemical Society, 136(19), 7058-7067 (2014-05-03)
The conversion of terminal alkynes to functionalized products by the direct addition of heteroatom-based nucleophiles is an important aim in catalysis. We report the design, synthesis, and mechanistic studies of the half-sandwich ruthenium complex 12, which is a highly active

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Herzon Group – Professor Product Portal

The Herzon group has developed highly active catalysts for the anti-Markovnikov hydration and reductive hydration of terminal alkynes to form aldehydes and linear alcohols, respectively.

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