901251

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

• Synonym(s): PPA directing group
• 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

Properties

• 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

Description

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable