期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 16, 页码 10913-10923出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01518
关键词
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资金
- National Key Research and Development Program of China [2016YFC1304704, 2018YFA0704000]
- Key Research Program of Frontier Sciences, CAS [QYZDY-SSWSLH018]
Trifluoromethylated compounds are usually obtained via trifluoromethylation reaction by the use of CF3SiMe3 and NaSO2CF3, Umemoto's and Togni's reagents. Here, an external fluorine anion-free direct deoxyhydrotrifluoromethylation of alpha-keto esters with a difluoromethylating reagent has been achieved, in which the employment of water can promote the dissociation of the CF2 group to form a CF3 moiety, which provides the successful transformation. The current protocol demonstrates one of the most practical approaches to generate alpha-trifluoromethyl esters with a broad substrate scope and high functional group compatibility, in which it is applicable to late-stage modification of biologically active compounds and can be readily scaled up. Mechanistic investigation reveals that an in situ-generated gem-difluoroalkene intermediate is decomposed by water, giving rise to acid fluoride and HF.
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