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Allylic amination of alkenes by tosyliminoiodobenzene: manganese porphyrins as suitable catalysts
Affiliation:1. Department of Physics, Henan Normal University, Xinxiang 453007, China;2. Physics Laboratory, North China University of Water Resources and Electric Power, Zhengzhou 450045, China;3. Department of Biochemistry, Case Western Reserve University, Cleveland, Ohio 44106;12. Department of Medicine, Case Western Reserve University, Cleveland, Ohio 44106;5. Department of Endocrinology and Metabolism, Tianjin Medical University General Hospital, Tianjin, Heping District, 300052 China;4. Division of Metabolism, Endocrinology and Diabetes, University of Michigan Medical Center, Ann Arbor, Michigan 48105, Australia;6. Department of Biochemistry and Molecular Biology, Indiana University School of Medicine, Indianapolis, Indiana 46202;1. Department of Chemistry, Ferdowsi University of Mashhad, International Campus, Mashhad 91775-1436, Iran;2. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran;3. Department of Food Processing, Food Science and Technology Research Institute, Iranian Academic Centre for Education, Culture, and Research: ACECR, Mashhad 91779, Iran;1. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., Moscow, 119991, Russian Federation;2. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China;1. Cátedra de Química General, Instituto de Química Inorgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000, Tucumán, Argentina;2. Laboratorio de Fotofísica y Espectroscopia Molecular, N°401, Av. Universidad #330, Campus Curauma, Valparaíso, Pontificia Universidad Católica de Valparaíso, Chile
Abstract:Manganese-porphyrins and particularly Mn(TPP)(ClO4) were found to be much better catalysts than iron-porphyrins for allylic N-tosylamination of alkenes by tosyliminoiodobenzene. With the former catalysts, cyclohexene was selectively transformed into 3-tosylaminocyclohexene with yields up to 70% and cis- and trans-hex-2-ene into allylic N-tosylamines with yields around 40%, whereas cyclooctene led to the corresponding allylic and homoallylic N-tosylamines.
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