title: Taming of fluoroform: direct nucleophilic trifluoromethylation of Si, B, S, and C centers.
abstract: Fluoroform (CF(3)H), a large-volume by-product of the manufacture of Teflon, refrigerants, polyvinylidene fluoride (PVDF), fire-extinguishing agents, and foams, is a potent and stable greenhouse gas that has found little practical use despite the growing importance of trifluoromethyl (CF3) functionality in more structurally elaborate pharmaceuticals, agrochemicals, and materials. Direct nucleophilic trifluoromethylation using CF(3)H has been a challenge. Here, we report on a direct trifluoromethylation protocol using close to stoichiometric amounts of CF(3)H in common organic solvents such as tetrahydrofuran (THF), diethyl ether, and toluene. The methodology is widely applicable to a variety of silicon, boron, and sulfur-based electrophiles, as well as carbon-based electrophiles.
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA 90089, USA. gprakash@usc.edu
authors.forename: G K Surya
authors.initials: GK
authors.lastname: Prakash
authors.forename: Parag V
authors.initials: PV
authors.lastname: Jog
authors.forename: Patrice T D
authors.initials: PT
authors.lastname: Batamack
authors.forename: George A
authors.initials: GA
authors.lastname: Olah
mesh_terms: D001895:Boron / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D017752:Greenhouse Effect; D008745:Methylation; D012825:Silicon / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
chemical_list: D005617:Chlorofluorocarbons, Methane; D005663:Furans; D012997:Solvents; C018674:tetrahydrofuran; D013455:Sulfur; D002244:Carbon; D001895:Boron; D012825:Silicon; C009554:fluoroform