901251
[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:
Molecular Weight:
200.19 (free base basis)
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
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form
powder or crystals
Quality Level
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
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.
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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
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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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