Design,scope and mechanism of highly active and selective chiral NHC–iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes |
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Authors: | Daven Foster Pengchao Gao Ziyun Zhang Gellrt Sipos Alexandre N Sobolev Gareth Nealon Laura Falivene Luigi Cavallo Reto Dorta |
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Institution: | Department of Chemistry, School of Molecular Sciences, University of Western Australia, M310, 35 Stirling Highway, 6009 Perth WA Australia.; King Abdullah University of Science and Technology (KAUST), Chemical and Life Sciences and Engineering, Kaust Catalysis Center, Thuwal 23955-6900 Saudi Arabia ; Centre for Microscopy, Characterisation and Analysis, University of Western Australia, 35 Stirling Highway, 6009 Perth WA Australia |
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Abstract: | Chiral, cationic NHC–iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and eliminated by using alternative reaction conditions. A detailed experimental and computational study on the reaction mechanism is performed providing valuable insights into the mode of action of the catalytic system and pointing to future modifications to be made for this catalytic platform.Chiral, cationic NHC–iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. |
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