title: Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.
abstract: A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Peter S
authors.initials: PS
authors.lastname: Thuy-Boun
authors.forename: Giorgio
authors.initials: G
authors.lastname: Villa
authors.forename: Devin
authors.initials: D
authors.lastname: Dang
authors.forename: Paul
authors.initials: P
authors.lastname: Richardson
authors.forename: Shun
authors.initials: S
authors.lastname: Su
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000478:Alkylation; D001565:Benzoates / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010648:Phenylacetates / Q000737:chemistry*
chemical_list: D001565:Benzoates; D001896:Boron Compounds; D008024:Ligands; D010648:Phenylacetates; D010165:Palladium; C025136:phenylacetic acid