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4-Dimethylaminopyridine-Boryl Radical Promoted Monodefluorinative Alkylation of 3,3-Difluorooxindoles

Chinese Journal of Chemistry 2022年第5期40卷 577-581页

作者： tesfaye tebeka simur Fentahun Wondu Dagnaw You-Jie Yu Feng-Lian Zhang Yi-Feng Wang Hefei National Laboratory for Physical at the Microscale Department of ChemistryUniversity of Science and Technology of China96 Jinzhai RoadHefeiAnhui230026 China

A selective monodefluorinative alkylation of 3,3-difluorooxindoles is achieved.The reaction starts by the attack of a 4-dimethylaminopyrine-boryl radical to the carbonyl oxygen atom of 3,3-difluorooxindoles,followed by a spin-center shift to generate radical intermediates with the elimination of a fluoride anion.The subsequent radical addition to alkenes affords a range of 3-alkyl-fluorooxindoles products.The strategy offers access to C-3 functionalized oxindoles with wide substrate scope and tolerates a wide range of functional groups.

关键词： Radical reactions Alkylation I Fluorine Spin-center shift Defluorination

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C–F bond functionalizations of trifluoromethyl groups via radical intermediates

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Chinese Chemical Letters 2022年第3期33卷 1193-1198页

作者： tesfaye tebeka simur Tian Ye You-Jie Yu Feng-Lian Zhang Yi-Feng Wang Department of Chemistry University of Science and Technology of ChinaHefei 230026China

Selective functionalization of C-F bonds in trifluoromethyl groups has recently received a growing interest, as it offers atom- and step-economic pathways to access highly valuable mono- and difluoroalkyl-substituted organic molecules using simple and inexpensive trifluoromethyl sources as the starting materials. In this regard, impressive progress has been made on the defluorinative functionalization reactions that proceed via radical intermediates. Nevertheless, it is still a great challenge to precisely control the defluorination process, due to the continuous decrease of the C-F bond strength after the replacement of one or two fluorine atoms with various functionalities. This review article is aimed to provide a brief overview of recently reported methods used to functionalize C-F bonds of CF_(3) groups via radical intermediates. An emphasis is placed on the discussion of mechanistic aspects and synthetic applications.

关键词： C–F bond functionalizations Radical intermediates Trifluoromethyl groups Difluorinated compounds Monofluorinated compounds

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