title: In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles.
abstract: A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K(3)PO(4) base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204, USA.
authors.forename: Ilya
authors.initials: I
authors.lastname: Popov
authors.forename: Hien-Quang
authors.initials: HQ
authors.lastname: Do
authors.forename: Olafs
authors.initials: O
authors.lastname: Daugulis
mesh_terms: D002244:Carbon / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011188:Potassium / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013455:Sulfur / Q000737:chemistry*
chemical_list: D006219:Halogens; D018020:Lithium Compounds; D013455:Sulfur; D002244:Carbon; D011188:Potassium