Synthesis of iridium complexes with new planar chiral chelating phosphinyl-imidazolylidene ligands and their application in asymmetric hydrogenation |
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| Affiliation: | 1. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China;2. Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan;3. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow 119991, Russia;4. Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;1. Jiangxi Engineering Laboratory of Waterborne Coatings, Jiangxi Science and Technology Normal University, Nanchang 330013, China;2. School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang, 330013, China;3. State key laboratory for marine corrosion and protection, Luoyang ship material research institute, Qingdao, 266101, China;1. College of Chemistry and Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, Xiangtan University, Xiangtan 411105, China;2. CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China |
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| Abstract: | The synthesis of planar chiral phosphinoimidazolium salts such as (Rp)-3-(4-diphenyl-phosphino[2.2]paracyclophan-12-ylmethyl)-1-(2,6-diisopropylphenyl)imidazolium bromide (Rp)-11c starting from enantiopure 4,12-dibromo[2.2]paracyclophane (Rp)-6 is reported. After deprotonation of these salts and a subsequent reaction with [Ir(COD)Cl]2, chelating iridium imidazolylidene complexes (Rp)-5a–c are obtained. These complexes catalyze the asymmetric hydrogenation of functionalized and simple alkenes with up to 89% ee. |
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