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901251

Sigma-Aldrich

[2,2′-Bipyridine]-6-carboxylic acid hydrochloride

Synonym(s):

PPA directing group

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About This Item

Empirical Formula (Hill Notation):
C11H8N2O2 · xHCl
CAS Number:
4392-87-4
Molecular Weight:
200.19 (free base basis)
MDL number:
MFCD11100046
UNSPSC Code:
12352101
NACRES:
NA.22

form

powder or crystals

Quality Level

100

reaction suitability

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

InChI

1S/C11H8N2O2/c14-11(15)10-6-3-5-9(13-10)8-4-1-2-7-12-8/h1-7H,(H,14,15)

InChI key

ZQTILGDVDYWICD-UHFFFAOYSA-N

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Application

Developed in the Engle lab, this 2,2′-bipyridylamide (PPA) is a pincer-like, removable tridentate directing group that stabilizes 6-membered palladacycles for olefin functionalization. Together with similar ligand PAQ (901250), 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.

Other Notes

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

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (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

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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.

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