Direct Hydrodefluorination of CF3-Alkenes via a Mild SN2' Process Using Rongalite as a Masked Proton Reagent

被引:25
作者
Chen, Xiang-Long [1 ]
Yang, Dong-Sheng [1 ]
Tang, Bo-Cheng [2 ]
Wu, Chun-Yan [1 ]
Wang, Huai-Yu [1 ]
Ma, Jin-Tian [1 ]
Zhuang, Shi-Yi [1 ]
Yu, Zhi-Cheng [1 ]
Wu, Yan-Dong [1 ]
Wu, An-Xin [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
[2] Hong Kong Polytech, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Kowloon, Hong Kong 999077, Peoples R China
基金
中国国家自然科学基金;
关键词
F BOND ACTIVATION; GEM-DIFLUOROALKENES; BIOLOGICAL-ACTIVITY; FLUORINE; TRIFLUOROMETHYL; FUNCTIONALIZATION; PHARMACEUTICALS; CONSTRUCTION; ALKYLATION; GENERATION;
D O I
10.1021/acs.orglett.3c00645
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and efficient hydrodefluorination process was developed for the synthesis of gem-difluoroalkenes. This reaction employs rongalite as a masked proton source and does not require any additional catalysts or reductants. Notably, trifluoromethyl alkenes having both terminal and internal double bonds are compatible with this process, allowing for a wider range of substrates. The successful late-stage functionalizations of pharmaceuticals and gram-scale syntheses were used to demonstrate the viability of this method.
引用
收藏
页码:2294 / 2299
页数:6
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