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Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers

文献类型：期刊论文

作者Wang, Zhen-Yu1; Zhang, Xu3; Chen, Wen-Qing3; Sun, Guo-Dong1,5; Wang, Xing1; Tan, Lin1,4,5; Xu, Hui1,3,5; Dai, Hui-Xiong1,2,3,4,5
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2024-02-12
页码7
关键词C-C Bond Cleavage Deacylation Regioselective Deuteration Difunctionalization Palladium Catalysis
ISSN号1433-7851
DOI10.1002/anie.202319773
通讯作者Xu, Hui(xuhui2018@simm.ac.cn) ; Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要We report herein the development of palladium-catalyzed deacylative deuteration of arylketone oxime ethers. This protocol features excellent functional group tolerance, heterocyclic compatibility, and high deuterium incorporation levels. Regioselective deuteration of some biologically important drugs and natural products are showcased via Friedel-Crafts acylation and subsequent deacylative deuteration. Vicinal meta-C-H bond functionalization (including fluorination, arylation, and alkylation) and para-C-H bond deuteration of electro-rich arenes are realized by using the ketone as both directing group and leaving group, which is distinct from aryl halide in conventional dehalogenative deuteration. A palladium-catalyzed deuteration of arylketone oxime ethers has been realized. Regioselective deuteration of some biologically important drugs and natural products is showcased via Friedel-Crafts acylation and subsequent deacylative deuteration. Vicinal difunctionalization of electro-rich arenes is achieved by using the ketone as both directing group and leaving group.+ image
WOS关键词C-H FUNCTIONALIZATION ; REDUCTIVE CLEAVAGE ; ARYL KETONES ; CARBON-CYANO ; BOND ; ACTIVATION ; TRITIATION ; COMPLEXES ; DEUTERIUM ; STRATEGY
资助项目National Natural Science Foundation of China ; Shanghai Institute of Materia Medica ; Chinese Academy of Sciences ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Science and Technology Commission of Shanghai Municipality[21ZR1475400] ; Science and Technology Commission of Shanghai Municipality[23ZR1474400] ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Program of Shanghai Academic Research Leader[19XD1424600] ; Shanghai Postdoctoral Excellence Program[2023706] ; Shanghai Postdoctoral Excellence Program[2022699] ; [22171276] ; [21920102003]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001160432500001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/309222]  
专题新药研究国家重点实验室
通讯作者Xu, Hui; Dai, Hui-Xiong
作者单位1.Chinese Acad Sci, Shanghai Inst Materia Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
3.Nanjing Univ Chinese Med, Sch Chinese Materia Med, Nanjing 210023, Jiangsu, Peoples R China
4.Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Zhen-Yu,Zhang, Xu,Chen, Wen-Qing,et al. Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024:7.
APA Wang, Zhen-Yu.,Zhang, Xu.,Chen, Wen-Qing.,Sun, Guo-Dong.,Wang, Xing.,...&Dai, Hui-Xiong.(2024).Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,7.
MLA Wang, Zhen-Yu,et al."Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2024):7.

入库方式： OAI收割

来源：上海药物研究所

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