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Dual ligands relay-promoted transformation of unstrained ketones to polyfluoroarenes and nitriles

Science China Chemistry 2023年第7期66卷 2037-2045页

作者： Zhen-Yu Wang Huiying Xu Xu Zhang Xing Wang Hui Xu Hui Gao Hui-Xiong Dai School of Chinese Materia Medica Nanjing University of Chinese MedicineNanjing 210023China CAS Key Laboratory of Receptor Research State Key Laboratory of Drug ResearchShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China School of Pharmaceutical Sciences Guangzhou Medical UniversityGuangzhou 511436China University of Chinese Academy of Sciences Beijing 100049China

C-C bond activation has emerged as a powerful tool for the construction of complex molecules.Herein,we report a dual ligands relay-promoted transformation of unstrained aryl,alkenyl and alkynyl ketones to the corresponding polyfluoroarenes and nitriles via C-C(=O)bond cleavage and subsequent decarboxylative arylation process.Various polyfluoroarene and nitrile products are obtained in one pot under cyanide-free conditions.The protocol features high atom economy,broad functional group tolerance and excellent heterocyclic compatibility.The late-stage functionalization of the drug and natural product demonstrated the synthetic utility of our protocol.Furthermore,the decisive role of the dual ligands was clarified and the mechanistic rationale including theβ-C elimination as the rate-limiting step was supported by detailed density functional theory(DFT)studies.

关键词： C-C bond activation dual ligands relay unstrained ketones modification of drugs and natural products DFT study

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Silver-catalyzed unstrained C(CO)–alkyl bond scission via[3+2]/retro-[3+2]cycloaddition of ketones with N-isocyanoiminotriphenylphosphorane

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Science China Chemistry 2021年第7期64卷 1157-1163页

作者： Zikun Wang Linxuan Li Xueying Zhang Xihe Bi Department of Chemistry Northeast Normal UniversityChangchun 130024China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

C(CO)–alkyl bonds are ubiquitous in a variety of organic molecules,and their selective activation and functionalization are important for the reconstruction of simple ketones into valuable building blocks.However,due to the thermodynamic and kinetic stability,the cleavage and transformation of the unstrained C(CO)–alkyl bonds remain a significant challenge.Herein,we report a novel silver-catalyzed scission of the unstrained C(CO)–alkyl bond of ketones by reacting with N-isocyanoiminotriphenylphosphorane(NIITP)under mild conditions.This method could transform a variety of unstrained ketones into iminophosphoranes and nitriles in high yields.Experimental and computational studies disclosed the reaction proceeded through an unprecedented[3+2]/retro-[3+2]cycloaddition mechanism.

关键词： silver-catalyzed C-C bond scission unstrained ketones tertiary alcohol intermediates cycloaddition

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