title: Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C-H Alkoxycarbonylation Reaction.
abstract: A PdII-catalyzed ortho C-H alkoxycarbonylation reaction of aryl silanes toward active hexafluoroisopropyl (HFIP) benzoate esters has been developed. This efficient reaction features high selectivity and good functional-group tolerance. Notably, given the general nature of the silyl-tethered directing group, this method delivers products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group, and it is thought to be crucial for the success of this alkoxycarbonylation reaction.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St., Room 4500, Chicago, IL, 60607, USA.
authors.forename: Yang
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St., Room 4500, Chicago, IL, 60607, USA.
authors.forename: Vladimir
authors.identifier: 0000-0002-7836-7596
authors.initials: V
authors.lastname: Gevorgyan
keywords: C−H activation; heterocycles; hydrogen bonds; palladium; silane