title: An Unconventional Mechanistic Insight into SCF3Formation from Difluorocarbene: Preparation of18F-Labeled α-SCF3Carbonyl Compounds.
abstract: Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the formation of thiocarbonyl fluoride and also enables transition-metal-mediated trifluoromethylthiolation and [18F]trifluoromethylthiolation of α-bromo carbonyl compounds with broad substrate scope and compatibility.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zheng
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin, 300072, China.|Division of Nuclear Medicine and Molecular Imaging and Gordon Center for Medical Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, 55 Fruit St., White 427, Boston, MA, USA.
authors.forename: Ran
authors.initials: R
authors.lastname: Cheng
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Jin-Hong
authors.initials: JH
authors.lastname: Lin
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Dong-Hai
authors.initials: DH
authors.lastname: Yu
authors.affiliation: Division of Nuclear Medicine and Molecular Imaging and Gordon Center for Medical Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, 55 Fruit St., White 427, Boston, MA, USA.
authors.forename: Longle
authors.initials: L
authors.lastname: Ma
authors.affiliation: Shanghai Institute of Applied Physics, Chinese Academy of Sciences, 2019 Jialuo Road, Shanghai, 201800, China.
authors.forename: Lina
authors.initials: L
authors.lastname: Jia
authors.affiliation: Shanghai Institute of Applied Physics, Chinese Academy of Sciences, 2019 Jialuo Road, Shanghai, 201800, China.
authors.forename: Lan
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Division of Nuclear Medicine and Molecular Imaging and Gordon Center for Medical Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, 55 Fruit St., White 427, Boston, MA, USA.
authors.forename: Lu
authors.initials: L
authors.lastname: Wang
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Ji-Chang
authors.initials: JC
authors.lastname: Xiao
authors.affiliation: Division of Nuclear Medicine and Molecular Imaging and Gordon Center for Medical Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, 55 Fruit St., White 427, Boston, MA, USA.
authors.forename: Steven H
authors.initials: SH
authors.lastname: Liang
keywords: 18F-labeling; difluorocarbene; fluorine; sulfuration; trifluoromethylthiolation