Direct palladium-catalyzed allylic alkylations of alcohols with enamines: Synthesis of homoallyl ketones |
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| Institution: | 1. Université de Tunis EL Manar, Faculté des Sciences, Laboratoire de Chimie Organique Structurale Campus Universitaire, 2092 Tunis, Tunisia;2. Institute for Research and Physicochemical Analysis (INRAP), Pôle Technologique, Sidi Thabet, Tunisia;3. Institut Parisien de Chimie Moléculaire (IPCM), UMR 8232 Sorbonne Universités, UPMC Univ Paris 06, CNRS 4 place Jussieu, 75005 Paris, France;1. Key Laboratory of Industrial Microbiology, Ministry of Education, College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, PR China;2. Tianjin Key Laboratory of Industry Microbiology, College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, PR China;3. Key Laboratory of Food Nutrition and Safety (Tianjin University of Science and Technology), Ministry of Education, Tianjin 300457, PR China;4. Obesita & Algaegen LLC, College Station, TX 77845, United States;5. Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire UMR CNRS 8232, 4 Place Jussieu, 75005 Paris, France;1. Laboratory of Spectroscopic Characterization and Optical Materials, University of Sfax, Faculty of Sciences, B.P. 1171, 3000, Sfax, Tunisia;2. Université de Sfax, Faculté des Sciences de Sfax, Département de Physique, Laboratoire de Physique Appliquée, Groupe de Physique des Matériaux Luminescent, Sfax, Tunisia;1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, PR China;2. State Key Lab of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, PR China |
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| Abstract: | An efficient, direct nucleophilic allylic substitution of α-, β- and γ-substituted alcohols with enamines, using the Pd(OAc)2/PPh3 catalyst system and ZnBr2 as a promoter in CH2Cl2 at reflux, is reported. The reaction course was dependent on the steric hindrance at the α- or γ-positions with respect to the functionalized α-carbon, selectively affording in moderate to good yields, α- or γ-homoallyl ketones, the so-called “linear” and “branched” products, respectively. |
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| Keywords: | Allylic substitution Homoallyl ketone Enamine Palladium Allylic alcohol |
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