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Merck
CN

901216

Sigma-Aldrich

(S)-Ph-quinox

≥95%

Synonym(s):

(S)-4-Phenyl-2-(quinolin-2-yl)-4,5-dihydrooxazole

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About This Item

Empirical Formula (Hill Notation):
C18H14N2O
CAS Number:
1252576-13-8
Molecular Weight:
274.32
UNSPSC Code:
12352200

Key Documents

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Assay

≥95%

form

powder or crystals

reaction suitability

reagent type: catalyst
reagent type: ligand
reaction type: C-H Activation

mp

142 °C

Application

(S)-Ph-quinox is a chiral dinitrogen ligand which is used in the iridium-catalyzed enantioselective borylation and silylation of aromatic C-H bonds, in addition to the enantioselective palladium-catalyzed diamination of alkenes. It can also be used in the aza-Wacker-type cyclization reaction of the olefinic tosylamides with molecular oxygen.

Other Notes

Enantioselective palladium-catalyzed diamination of alkenes using N-fluorobenzenesulfonimide

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Pd-catalyzed asymmetric aza-Wacker-type cyclization reaction of olefinic tosylamides.
Jiang F, et al.
Tetrahedron Letters, 51(39), 5124-5126 (2010)
Enantioselective Borylation of Aromatic C? H Bonds with Chiral Dinitrogen Ligands.
Su B, et al.
Angewandte Chemie (International Edition in English), 56(25), 7205-7208 (2017)
A Chiral Nitrogen Ligand for Enantioselective, Iridium?Catalyzed Silylation of Aromatic C? H Bonds.
Su B, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 129(4), 1112-1116 (2017)
Erica L Ingalls et al.
Journal of the American Chemical Society, 135(24), 8854-8856 (2013-06-06)
An enantioselective Pd-catalyzed vicinal diamination of unactivated alkenes using N-fluorobenzenesulfonimide as both an oxidant and a source of nitrogen is reported. The use of Ph-pybox and Ph-quinox ligands afforded differentially protected vicinal diamines in good yields with high enantioselectivities. Mechanistic

Articles

QuinoxP*

QuinoxP*: Air-Stable and Highly Efficient and Productive Chiral Ligands

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