title: Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3.
abstract: A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organotrifluoroborates, MnF3, and a Pd(II) catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 °C in weakly acidic media), are effective for installing methyl and 1° alkyl groups, and do not require promoters such as benzoquinone.
authors.affiliation: Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
authors.forename: Sharon R
authors.initials: SR
authors.lastname: Neufeldt
authors.forename: Cydney K
authors.initials: CK
authors.lastname: Seigerman
authors.forename: Melanie S
authors.initials: MS
authors.lastname: Sanford
mesh_terms: D000478:Alkylation; D016227:Benzoquinones / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D006860:Hydrogen Bonding; D008024:Ligands; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*
chemical_list: D016227:Benzoquinones; D001881:Borates; D008024:Ligands; D005461:Fluorine; D008345:Manganese; D010165:Palladium; D011188:Potassium