title: Palladium-Catalyzed Direct Arylation of C(sp(3))-H Bonds of α-Cyano Aliphatic Amides.
abstract: Pd(OAc)2-catalyzed arylation of C(sp(3))-H bonds in α-cyano-α-methyl aliphatic amides is achieved in the presence of 8-aminoquinoline, as a removable directing group, using Mn(OAc)2 and Na2CO3. The current strategy enables the placement of an aryl/heteroaryl group at the β-position of α-cyano aliphatic acids for the first time. Wide functional group tolerance and easily accessible starting materials provide an efficient protocol for the synthesis of arylated α-cyano amides. Furthermore, the synthetic utility of the products has been demonstrated by their efficient conversions to medicinally important α,α-dialkylated acid and β-amino acid derivatives.
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, Union University , Jackson, Tennessee 38305, United States.
authors.forename: M Damoder
authors.initials: MD
authors.lastname: Reddy
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, Union University , Jackson, Tennessee 38305, United States.
authors.forename: E Blake
authors.initials: EB
authors.lastname: Watkins
mesh_terms: D000577:Amides / Q000737:chemistry*; D000634:Aminoquinolines / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000577:Amides; D000634:Aminoquinolines; D009570:Nitriles; D010165:Palladium; C080436:8-aminoquinoline