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Catalyst Control in Switching the Site Selectivity of C−H Olefinations of 1,2-Dihydroquinolines: An Approach to Positional-Selective Functionalization of Quinolines |
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| Authors: | Dr. Riki Das Nandkishor Prakash Khot Akanksha Santosh Deshpande Dr. Manmohan Kapur |
| Affiliation: | 1. Department of Chemistry, Indian Institution of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462066 MP, India Present address: Department of Chemistry, University of Minnesota, Minneapolis, MN, 55455-0431 USA These authors contributed equally to this work.;2. Department of Chemistry, Indian Institution of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462066 MP, India These authors contributed equally to this work.;3. Department of Chemistry, Indian Institution of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462066 MP, India |
| Abstract: | A unique approach to achieve site-selective C−H olefinations exclusively at the C-3- or C-8-positions in the quinoline framework has been developed by catalyst control. Distal C(3)−H functionalization is achieved by using palladium catalysis, whereas proximal C(8)−H functionalization is obtained by employing ruthenium catalysis. Switching the site selectivity within a single substrate directly indicates two diverse pathways, which are operating under the palladium- and ruthenium-catalyzed reaction conditions. |
| Keywords: | C−H functionalization directing groups quinolines site selectivity transition-metal catalysis |