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Alcohols controlled selective radical cyclization of 1,6-dienes under mild conditions
Affiliation:1. State Key Laboratory Base of Novel Functional Materials and Preparation Science, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, China;2. Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China;3. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China;1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, China;2. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Department of Chemistry, Nanchang University, Nanchang 330031, China;2. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China;1. College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, China;2. School of Life Sciences and Chemistry, Hunan University of Technology, Zhuzhou 412007, China;3. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China;1. Department of Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, China;2. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China;3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;4. School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China
Abstract:An efficient procedure for the selective preparation of hydroxy-, carbonyl- and acetal-containing 2-pyrrolidinones has been developed through radical cyclization of 1,6-dienes initiated by α-C(sp3)–H functionalization of alcohols. This protocol could be conducted at catalyst-free conditions at relatively low temperature (80 °C) by employing commercially available tert-butyl peroxybenzoate (TBPB) as the oxidant.
Keywords:Green chemistry  Metal free  Cyclization  Alcohol  Pyrrolidinone
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