title: Synthesis of α,β-Unsaturated N-Aryl Ketonitrones from Oximes and Diaryliodonium Salts: Observation of a Metal-Free N-Arylation Process.
abstract: An efficient transition-metal-free method for the preparation of α,β-unsaturated N-aryl ketonitrones under mild conditions has been developed. This reaction shows good functional group tolerance for both electron-rich and electron-deficient substituents on both oximes and diaryliodonium salts. Two examples of gram-scale preparations have been realized in good yields. Further transformations of these nitrones to different N-heterocycles have been demonstrated. DFT calculations suggest that N-arylation products are formed by [1,3]-phenyl migration of an O-coordinated oximate complex via a four-centered transition state, while the O-arylation products are formed by [1,3]-phenyl migration of a N-coordinated oximate complex.
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Xiao-Pan
authors.initials: XP
authors.lastname: Ma
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Wei-Min
authors.initials: WM
authors.lastname: Shi
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Xue-Ling
authors.initials: XL
authors.lastname: Mo
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Xiao-Hua
authors.initials: XH
authors.lastname: Li
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Liang-Gui
authors.initials: LG
authors.lastname: Li
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Cheng-Xue
authors.initials: CX
authors.lastname: Pan
authors.affiliation: Department of Chemistry and Chemical Biology, Cornell University , Ithaca, New York 14853, United States.
authors.forename: Bo
authors.initials: B
authors.lastname: Chen
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Gui-Fa
authors.initials: GF
authors.lastname: Su
authors.affiliation: Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, People's Republic of China.
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Mo