title: Facile Syntheses of N-Heterocyclic Carbene Precursors through I2 - or NIS-Promoted Amidiniumation of N-Alkenyl Formamidines.
abstract: We have developed I2 - or N-iodosuccinimide (NIS)-mediated amidiniumation of N-alkenyl formamidines for the syntheses of cyclic formamidinium salts, some of which could be directly used as N-heterocyclic carbene (NHC) precursors. Treatment of iodine-containing formamidinium salts with Al2 O3 led to the formation of cyclic formamidinium salts with an unsaturated backbone. A rhodium(I) complex ligated by a representative NHC was prepared by the reaction of [Rh(cod)Cl]2 (cod=1,5-cyclooctadiene) with the free carbene obtained in situ from deprotonation of the corresponding formamidinium salts. The NHCs prepared in situ can also react with S8 to afford the corresponding thiones.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai, 200237, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai, 200237, China.
authors.forename: Jiajun
authors.initials: J
authors.lastname: Jiao
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai, 200237, China.
authors.forename: Caiyun
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai, 200237, China.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, China.
authors.forename: Min
authors.initials: M
authors.lastname: Shi
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai, 200237, China. zhangj@ecust.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Zhang
mesh_terms: D000578:Amidines / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013388:Succinimides / Q000737:chemistry*
chemical_list: D000578:Amidines; D006571:Heterocyclic Compounds; D013388:Succinimides; C030011:carbene; C008155:N-iodosuccinimide; C077922:formamidine; D007455:Iodine; D008697:Methane
keywords: N-heterocyclic carbenes; N-iodosuccinimide; alkenes; iodine; iodoamination