期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 10, 期 3, 页码 485-495出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000723
关键词
Trifluoromethyl; Difluoromethyl; Cyclopropanes; Carbenes; Fluorine
资金
- National Natural Science Foundation [21971252, 21991122, 22065004]
- Key Research Program of Frontier Sciences, Chinese Academy of Sciences (CAS) [QYZDJSSW-SLH049]
- Youth Innovation Promotion Association CAS [2019256]
- Joint Science and Technology Funds of the Youth Growth S&T Personnel Foundation of Guizhou Education Department [KY[2019]101]
- Discipline and Master's Site Construction Project of Guiyang University by Guiyang City Financial Support Guiyang University [HC-2020]
- Shanghai Research Institute of Chemical Industry Co., Ltd. [SKL-LCTP-201802]
- Innovation Academy for Green Manufacture-CAS [IAGM2020C01]
Efforts have been directed towards developing efficient methods for the construction of CF3- or HCF2-substituted cyclopropanes in pharmaceutical and agrochemical applications. CF3-cyclopropanes are typically synthesized by transition metal-catalyzed cyclopropanation of alkenes, while the synthesis of HCF2-cyclopropanes remains largely unexplored with some difluoromethylcarbene reagents being developed for potential application. These methods may find utility in the synthesis of biologically active molecules.
CF3- or HCF2-substituted cyclopropanes are of great interest in pharmaceutical chemistry and agrochemistry, and thus significant efforts have been directed towards the development of efficient methods for the installation of these motifs. This Minireview summarizes recent efforts for the construction of CF3- or HCF2-substituted cyclopropanes. CF3-cyclopropanes are usually synthesized by a transition-metal-catalyzed cyclopropanation of alkenes with a trifluoromethylcarbene generated in situ from a diazocompound, CF3CHN2 or CF3C(Ar)N-2. The synthesis of HCF2-cyclopropanes remains largely unexplored. Some difluoromethylcarbene reagents have been developed, such as HCF2CHN2, Ph2S+CH2CF2H TfO-, and difluoroacetaldehyde N-triftosylhydrazone (DFHZ-Tfs), and cyclopropanation of alkenes with these reagents could also occur by transition metal catalysis. These protocols may find great utility in the synthesis of biologically active molecules.
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