Epoxidation of alkenes catalyzed by cobalt(II) calix[4]pyrrole |
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| Affiliation: | 1. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;2. Program of Petrochemistry and Polymer Science, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;1. Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan;2. National Synchrotron Radiation Research Center, Hsinchu 30076, Taiwan;3. Center for General Education, Chang Gung University, Taoyuan City 33302, Taiwan;4. Department of Pathology, Chang Gung Memorial Hospital, Taoyuan City 33302, Taiwan;5. Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013, Taiwan;1. Department of Chemistry, C.U. Shah University, Wadhwan 363030, India;2. Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad 380009, India;1. Analytical Discipline and Centralized Instrument Facility, CSIR-Central Salt and Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar 364002, India;2. Academy of Scientific and Innovative Research-CSMCRI, Gijubhai Badheka Marg, Bhavnagar 364002, India;1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, PR China;2. College of Chemistry and Material Engineering, Chaohu University, Chaohu, 238000, PR China;1. Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 275, 69120 Heidelberg, Germany |
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| Abstract: | The new developed epoxidation system utilizing cobalt(II) calix[4]pyrrole as a catalyst in the aldehyde/oxygen as an oxidant was explored. Six calix[4]pyrrole ligands were synthesized and the well characterized ligands were complexed with Co(II) salts. It was disclosed that Co(II) meso-tetrakis (4-methoxyphenyl)-tetramethyl calix[4]pyrrole revealed the best catalytic performance to provide the corresponding epoxide in high yields with excellent selectivity under mild conditions. In addition, the stereoselectivity and regioselectivity studies of the system using cis- and trans-stilbenes and 4-vinylcyclohexene, as chemical probes were thoroughly investigated. |
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