A General Protocol toward Oxindoles Bearing C_(3)-Allylic Quaternary Stereocenter via Domino Reaction:A Concise Synthesis of Heterocycle-Fused Indoline Alkaloids  

作　　者：Hanxiao Yang Ruoqian Fan Daheng Wen Mengmeng Fan Weiwei Fang 

机构地区：[1]Jiangsu Co-lnnovation Center of Efficient Processing and Utilization of Forest Resources,International Innovation Center for Forest Chemicals and Materials,College of Chemical Engineering,Nanjing ForestryUniversity,159 Longpan Road,Nanjing,Jiangsu 210037,China [2]Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials,Department of Chemistry,Fudan University,Shanghai 200438,China

出　　处：《Chinese Journal of Chemistry》2024年第20期2459-2465,共7页中国化学（英文版）

基　　金：National Natural Science Foundation of China(No.22101133);Natural Science Foundation of Jiangsu Province(No.BK20200768)and Nanjing Forestry University are greatly acknowledged.

摘　　要：An efficiently catalytic method toward the synthesis of indolin-2-ones featuring an allylic derived C_(3)-quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N-substituted-N-(2-bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene(AnIPr)-ligated oxazoline palladacycle.It enabled a very broad substrate scope tolerating different functional groups,electronic properties and steric bulkiness.Notably,it revealed a great potential to build diverse heterocycle-fused indoline alkaloids via the same intermediate 3-allyl-1,3-dimethylindolin-2-one.

关 键 词：C3-Allylic quaternary stereocenter 3 3'-Disubstituted oxindoles Domino reaction Indoline alkaloids Molecular diversity Nitrogen heterocycles Organohalides Palladacyclic N-heterocyclic carbene 

分 类 号：O62[理学—有机化学]