Facile Syntheses of N‐Heterocyclic Carbene Precursors through I2‐ or NIS‐Promoted Amidiniumation of N‐Alkenyl Formamidines |
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| Authors: | Jing Li Jiajun Jiao Caiyun Zhang Prof?Dr Min Shi Dr Jun Zhang |
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| Affiliation: | 1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry&Molecular Engineering, East China University of Science and Technology, Shanghai, China;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China |
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| 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 Al2O3 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. |
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| Keywords: | alkenes iodine iodoamination N-heterocyclic carbenes N-iodosuccinimide |
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