title: Redox-Neutral Rhodium-Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion.
abstract: A synthetic protocol for the expedient construction of 5-methylene-1H-pyrrol-2(5H)-one derivatives through rhodium-catalyzed [4+1] annulation with gem-difluoroacrylate as the C1component was reported. By taking advantage of the twofold C-F bond cleavage occurring during the annulation, this reaction not only allows the synthesis of these heterocyclic compounds under overall oxidant-free conditions but also renders the transformation stereospecific. The very mild reaction conditions employed ensure compatibility with a wide variety of synthetically useful functional groups.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, P.R. China.|Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, Jiangsu, 210009, P.R. China.
authors.forename: Huan
authors.initials: H
authors.lastname: Liu
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, P.R. China.|Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, Jiangsu, 210009, P.R. China.
authors.forename: Shengjin
authors.initials: S
authors.lastname: Song
authors.affiliation: Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, Jiangsu, 210009, P.R. China.
authors.forename: Cheng-Qiang
authors.initials: CQ
authors.lastname: Wang
authors.affiliation: Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, Jiangsu, 210009, P.R. China.
authors.forename: Chao
authors.initials: C
authors.lastname: Feng
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, P.R. China.|Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 637371, Singapore.
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D012238:Rhodium
keywords: C−H activation; amides; annulation; fluoroalkenes; rhodium