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

文献类型：期刊论文

作者Wang, Zhen-Yu1; Xu, Huiying3; Zhang, Xu1; Wang, Xing2; Xu, Hui2; Gao, Hui3; Dai, Hui-Xiong1,2,4
刊名SCIENCE CHINA-CHEMISTRY
出版日期2023-07-01
卷号66期号:7页码:2037-2045
ISSN号1674-7291
关键词C-C bond activation dual ligands relay unstrained ketones modification of drugs and natural products DFT study
DOI10.1007/s11426-023-1653-3
通讯作者Xu, Hui(xuhui2018@simm.ac.cn) ; Gao, Hui(gaoh9@gzhmu.edu.cn) ; Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要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 the & beta;-C elimination as the rate-limiting step was supported by detailed density functional theory (DFT) studies.
WOS关键词ELECTRON-DEFICIENT POLYFLUOROARENES ; PALLADIUM-CATALYZED CYANATION ; SINGLE BOND-CLEAVAGE ; C-H OLEFINATION ; BIARYL SYNTHESIS ; AROMATIC CARBOXYLATES ; DIRECT ARYLATION ; ALPHA-ARYLATION ; ARYL KETONES ; OXIMES
资助项目Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; National Natural Science Foundation of China[21772211] ; National Natural Science Foundation of China[21920102003] ; Institutes for Drug Discovery and Development, Chinese Academy of Sciences[CASIMM0120163006] ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science amp; Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006] ; China Postdoctoral Science Foundation[2019M662854]
WOS研究方向Chemistry
语种英语
出版者SCIENCE PRESS
WOS记录号WOS:001017587400002
源URL[http://119.78.100.183/handle/2S10ELR8/306695]  
专题新药研究国家重点实验室
通讯作者Xu, Hui; Gao, Hui; Dai, Hui-Xiong
作者单位1.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, State Key Lab Drug Res, Shanghai 201203, Peoples R China
3.Guangzhou Med Univ, Sch Pharmaceut Sci, Guangzhou 511436, Peoples R China
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Zhen-Yu,Xu, Huiying,Zhang, Xu,et al. Dual ligands relay-promoted transformation of unstrained ketones to polyfluoroarenes and nitriles[J]. SCIENCE CHINA-CHEMISTRY,2023,66(7):2037-2045.
APA Wang, Zhen-Yu.,Xu, Huiying.,Zhang, Xu.,Wang, Xing.,Xu, Hui.,...&Dai, Hui-Xiong.(2023).Dual ligands relay-promoted transformation of unstrained ketones to polyfluoroarenes and nitriles.SCIENCE CHINA-CHEMISTRY,66(7),2037-2045.
MLA Wang, Zhen-Yu,et al."Dual ligands relay-promoted transformation of unstrained ketones to polyfluoroarenes and nitriles".SCIENCE CHINA-CHEMISTRY 66.7(2023):2037-2045.

入库方式： OAI收割

来源：上海药物研究所

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