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Multi-component reactions via copper(I) difluorocarbene as carbonyl source for constructing α-aminoamide derivatives

文献类型：期刊论文

作者Li, Jiuling4,5; Wang, Baofan4; Liu, Taichen3,5; Wen, Qinghong4; Jing, Tongfei4; Fu, Xiang2; Pan, Yingming3; Wei, Kai5; Zhou, Xiaoyu1; Hu, Wenhao2
刊名NATURE COMMUNICATIONS
出版日期2025-07-18
卷号16期号:1页码:10
DOI10.1038/s41467-025-61947-z
通讯作者Li, Jiuling(orgchem90@163.com) ; Zhou, Xiaoyu(zhouxiaoyu@tzc.edu.cn) ; Kang, Zhenghui(kangzhenghui@simm.ac.cn)
英文摘要Difluorocarbene, an important reactive intermediate in organic synthesis, exhibits intriguing properties and synthetic versatility. However, great challenges in modulating reaction pathways limit its widespread application in synthetic chemistry. While metal-catalyzed difluorocarbene transfer offers a promising strategy but remains a formidable challenge. Herein, we disclose a copper-mediated multicomponent reaction of amine, aldehyde and BrCF2CO2K for synthesis of alpha- aminoamide derivatives, wherein copper-difluorocarbene serve as carbonyl source. Control experiments and DFT calculations support the pathway initiated by formation of a copper-difluorocarbene from BrCF2CO2K, followed by nucleophilic attack of the amine to produce an ammonium ylide, interception of the ylide with imine, and defluorination via carbonyl migration. This transformation demonstrates broad substrate scope, accommodating not only aromatic aldehydes but also alkyl aldehydes and drug-modified arylamines, highlighting its synthetic applicability. Furthermore, the method provides a practical and ideal alternative to classical Ugi or Strecker reactions, circumventing the need for toxic cyanide salts or unstable isonitriles.
WOS关键词DIFLUOROMETHYLATED ARENES ; DIAZO-COMPOUNDS ; FLUORINE ; ALCOHOLS ; ACCESS ; ETHERS ; (TRIFLUOROMETHYL)COPPER ; PHARMACEUTICALS ; CYCLOPROPANES ; METATHESIS
资助项目Natural Science Foundation of Henan Province (Henan Province Natural Science Foundation)[2023A1515110403] ; Natural Science Foundation of Henan Province (Henan Province Natural Science Foundation)[2024A1515030037] ; Natural Science Foundation of Guangdong Province[2023M743925] ; China Postdoctoral Science Foundation[242300420201] ; China Postdoctoral Science Foundation[252300420796] ; Natural Science Foundation of Henan Province[LQN25B020014] ; Natural Science Foundation of Zhejiang Province
WOS研究方向Science & Technology - Other Topics
语种英语
WOS记录号WOS:001532066300015
出版者NATURE PORTFOLIO
源URL[http://119.78.100.183/handle/2S10ELR8/318864]  
专题中国科学院上海药物研究所
通讯作者Li, Jiuling; Zhou, Xiaoyu; Kang, Zhenghui
作者单位1.Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou, Peoples R China
2.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou, Peoples R China
3.Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, Guilin, Peoples R China
4.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan, Peoples R China
5.Pingdingshan Univ, Sch Med Sci, Pingdingshan, Peoples R China
推荐引用方式
GB/T 7714		 Li, Jiuling,Wang, Baofan,Liu, Taichen,et al. Multi-component reactions via copper(I) difluorocarbene as carbonyl source for constructing α-aminoamide derivatives[J]. NATURE COMMUNICATIONS,2025,16(1):10.
APA Li, Jiuling.,Wang, Baofan.,Liu, Taichen.,Wen, Qinghong.,Jing, Tongfei.,...&Kang, Zhenghui.(2025).Multi-component reactions via copper(I) difluorocarbene as carbonyl source for constructing α-aminoamide derivatives.NATURE COMMUNICATIONS,16(1),10.
MLA Li, Jiuling,et al."Multi-component reactions via copper(I) difluorocarbene as carbonyl source for constructing α-aminoamide derivatives".NATURE COMMUNICATIONS 16.1(2025):10.

入库方式： OAI收割

来源：上海药物研究所

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