期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 27, 期 32, 页码 8288-8294出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100672
关键词
C− F bond transformation; catalysis; fluorinated heterocycles; gem-difluoroalkene; indium
资金
- JST CREST, Japan [JPMJCR20R3]
- JSPS KAKENHI [JP18 K19079, JP18H01977, JP19 K05455]
Fluorinated heterocycles have been a focus in the pharmaceutical and agrochemical industries, with various strategies developed for their synthesis. Challenges still remain in the synthesis of fluorinated isocoumarin derivatives. A recent study reported the successful synthesis of diverse fluorinated isocoumarins using indium-catalyzed C-F bond transformation, with the reaction proceeding smoothly with inexpensive reagents.
Fluorinated heterocycles have attracted much attention in the pharmaceutical and agrochemical industries. Many strategies have already been developed to achieve the synthesis of fluorinated heterocycles. Formidable challenges remain, however, in the synthesis of fluorinated isocoumarin derivatives that are among the most alluring structural motifs. Herein, the indium-catalyzed C-F bond transformation of 2-(2,2-difluorovinyl) benzoates is reported, which are readily accessible compounds, to give a diverse array of fluorinated isocoumarins. The present reaction proceeds smoothly using inexpensive reagents: a catalytic amount of indium salt in the presence of zinc salt. A theoretical calculation of potential energy profiles showed that the reaction consists of oxymetalation with the elimination of alkyl halide and the beta-fluorine elimination.
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