Nucleophilic trifluoromethoxylation of alkyl halides without silver

被引:50
作者
Li, Yan [1 ,2 ]
Yang, Yang [1 ,2 ]
Xin, Jinrui [1 ,2 ]
Tang, Pingping [1 ,2 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elernentoorgan Chem, Tianjin 300071, Peoples R China
关键词
ALPHA-FLUORINATED ETHERS; MEDICINAL CHEMISTRY; TRIFLUOROMETHYLATION; THIOETHERS; REACTIVITY; REAGENT; AMINES;
D O I
10.1038/s41467-020-14598-1
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The biological properties of molecules containing the trifluoromethoxy group have made these compounds important targets in pharmaceuticals and agrochemicals, yet their preparation is still a substantial challenge. Herein, we present a practical nucleophilic trifluoromethoxylation of alkyl halides with (E)-O-trifluoromethyl-benzaldoximes (TFBO) as a trifluoromethoxylation reagent in the absence of silver under mild reaction conditions. The trifluoromethoxylation reagent TFBO is easily prepared and thermally stable, and can release CF3O- species in the presence of a base. Furthermore, broad scope and good functional group compatibility are demonstrated by application of the method to the late-stage trifluoromethoxylation of alkyl halides in complex small molecules.
引用
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页数:7
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