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Merck
CN

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

Key Documents

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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

SMILES string

n1c(cccc1C(=O)O)c2ncccc2

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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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