American Chemical Society
jo9b01808_si_003.cif (391.25 kB)

Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds

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posted on 2019-08-05, 13:33 authored by Lin Tang, Zhen Yang, Jingchao Jiao, Ying Cui, Guodong Zou, Qiuju Zhou, Yuqiang Zhou, Weihao Rao, Xiantao Ma
By altering the amount of Selectfluor, the highly selective mono- and difluorination of 1,3-dicarbonyl compounds has been achieved, affording a variety of 2-fluoro- and 2,2-difluoro-1,3-dicarbonyl compounds in good to excellent yields. The reaction can be readily performed in aqueous media without any catalyst and base, which features practical and convenient fluorination. Importantly, a gram-scale reaction, transformation of 2-fluoro-1,3-diphenylpropane-1,3-dione to 4-fluoro-1,3,5-triphenyl-1H-pyrazole, and chlorination and bromination of 1,3-dicarbonyl compounds are realized to further exhibit its synthetic utility.