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Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers.
Wang, Zhen-Yu; Zhang, Xu; Chen, Wen-Qing; Sun, Guo-Dong; Wang, Xing; Tan, Lin; Xu, Hui; Dai, Hui-Xiong.
Affiliation
  • Wang ZY; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
  • Zhang X; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, Jiangsu, 210023, China.
  • Chen WQ; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, Jiangsu, 210023, China.
  • Sun GD; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
  • Wang X; University of Chinese Academy of Sciences, Beijing, 100049, China.
  • Tan L; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
  • Xu H; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
  • Dai HX; School of Pharmaceutical Science and Technology, Hangzhou Institute of Advanced Study, Hangzhou, 310024, China.
Angew Chem Int Ed Engl ; 63(12): e202319773, 2024 Mar 18.
Article in En | MEDLINE | ID: mdl-38279666
ABSTRACT
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2024 Document type: Article Affiliation country: China Country of publication: Germany
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2024 Document type: Article Affiliation country: China Country of publication: Germany