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An Enantioselective Bidentate Auxiliary Directed Palladium-Catalyzed Benzylic C−H Arylation of Amines Using a BINOL Phosphate Ligand
Ist Teil von
Angewandte Chemie (International ed.), 2016-12, Vol.55 (49), p.15387-15391
Auflage
International ed. in English
Ort / Verlag
Germany: Blackwell Publishing Ltd
Erscheinungsjahr
2016
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
A new enantioselective palladium(II)‐catalyzed benzylic C−H arylation reaction of amines is enabled by the bidentate picolinamide (PA) directing group. This reaction provides the first example of enantioselective benzylic γ‐C−H arylations of alkyl amines, and proceeds with up to 97 % ee. The 2,2′‐dihydroxy‐1,1′‐binaphthyl (BINOL) phosphoric acid ligand, Cs2CO3, and solvent‐free conditions are essential for high enantioselectivity. Mechanistic studies suggest that multiple BINOL ligands are involved in the stereodetermining C−H palladation step.
Seeking direction: A new enantioselective palladium(II)‐catalyzed benzylic C−H arylation of amines is enabled by the bidentate picolinamide (PA) directing group. The BINOL phosphoric acid ligand, Cs2CO3, and solvent‐free conditions are essential for high enantioselectivity. Mechanistic studies indicate that multiple BINOL ligands are involved in the stereodetermining C−H palladation step.