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Silver-Mediated N-Trifluoromethylation of Amides and Peptides

查看全文 作  者:Zhenzhen [1]Zhang;Jiayan [1]He;Lin [1]Zhu;Haiwen [1]Xiao;Yewen [2]Fang;Chaozhong [1,2]Li 高影响力作者 机构地区:[1]Key Laboratory of Organofluorine Chemistry,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Road,Shanghai 200032,China;[2]School of Materials and Chemical Engineering,Ningbo University of Technology,201 Fenghua Road,Ningbo,Zhejiang 315211,China高影响力机构 出  处:《Chinese Journal of Chemistry》索引2020年第38卷第9期,共5页高影响力期刊 基  金:This project was supported by the National Natural Science Foundation of China(Grants Nos.21421002,21532008,21871285 and 21971253);the Chinese Academy of Sciences(Grants Nos.XDB20020000 and ZDB5-LY-SLH026);the Zhejiang Provincial Natural Science Foundation of China(Grant No.LY20B020008). 摘  要:Summary of main observation and conclusion We report herein the direct N-trifluoromethylation of N-H amides.Promoted by AgOTf and 2-fluoro-pyridine,the reaction of a variety of amides with Selectfluor,TMSCF3 and CsF proceeds smoothly at room temperature leading to the corresponding N-trifluoromethylated products in satisfactory yields.The protocol is also applicable to amino acid derivatives,resulting in efficient and chemoselective W-trifluoromethylation of di-and tri-peptides with retention of configuration.A mechanism involving reductive elimination of Ag(Ⅲ)intermediates to form N—CF3 bonds is proposed. 关 键 词:smoothly BONDS ELIMINATION
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