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901250

Sigma-Aldrich

2-(Pyridin-2-yl)quinolin-8-amine dihydrochloride

Synonym(e):

PAQ directing group

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About This Item

Empirische Formel (Hill-System):
C14H11N3 · 2HCl
Molekulargewicht:
294.18
UNSPSC-Code:
12352101

Assay

≥95%

Form

powder or crystals

Eignung der Reaktion

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

Anwendung

Developed in the Engle lab, this 2-pyridyl-8-aminoquinoline (PAQ) auxiliary is a pincer-like, removable tridentate directing group that stabilizes 6-membered palladacycles for olefin functionalization. Together with similar ligand PPA (901251), researchers demonstrated regioselective remote hydrocarbofunctionalization of alkene-containing substrate classes (e.g. 4-pentenoic acids, allylic alcohols, homoallyl amines, bis-homoallylamines) using Pd(II) catalysis.

Sonstige Hinweise

Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

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Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Miriam L O'Duill et al.
Journal of the American Chemical Society, 139(44), 15576-15579 (2017-10-04)
Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic

Verwandter Inhalt

Engle Group – Professor Product Portal

The Engle lab strives to invent novel catalytic alkene and alkyne functionalization methods to expedite organic synthesis. These transformations offer a powerful platform for conversion of simple, abundant, and planar starting materials into densely functionalized, stereochemically complex products in a single step. To this end, the Engle lab has developed various substrate directivity strategies in which native functional groups can be temporarily masked with auxiliaries that are capable of reversibly binding the metal catalyst, thereby enhancing kinetic reactivity, suppressing unwanted side reactions, and facilitating high selectivity. The Engle lab works with us to make synthetically enabling directing groups, catalysts, and ligands readily available to the synthetic community for reaction discovery and small-molecule synthesis.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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