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Visible-Light-Driven Direct 2,2-Difluoroacetylation Using an Organic Pigment Catalyst
ACS Sustainable Chemistry & Engineering ( IF 8.4 ) Pub Date : 2020-04-16 , DOI: 10.1021/acssuschemeng.0c01243
Yuji Furukawa , Masayuki Hayashi , Shuichi Hayase , Toshiki Nokami , Toshiyuki Itoh

Ethyl 2-bromo-2,2-difluoroacetate reacted with alkenes during irradiation by a blue light-emitting diode (LED; 470 nm) in the presence of 10 mol % fluorescein to achieve the visible-light-driven direct 2,2-difluoroacetylation; the combination of N,N,N,N-tetramethylethylenediamine (TMEDA) as a reducing agent and 1-methyl-2-pyrrolidinone (NMP) as a solvent was essential to afford the desired 2,2-difluoroacetyl compounds, and 10 types of 2,2-difluoroalkanoates were obtained in moderate to excellent yields. The same reaction conditions were applicable to the 2,2-difluoroacetylation of alkynes to attain 10 types of 2,2-difluoroalkenoates in moderate to excellent yields.

中文翻译:

使用有机颜料催化剂的可见光驱动直接2,2-二氟乙酰化

2-溴-2,2-二氟乙酸乙酯在蓝色发光二极管(LED; 470 nm)的照射下,在10 mol%荧光素的存在下与烯烃反应,从而实现可见光驱动的直接2,2-二氟乙酰化; 的组合ÑÑÑÑ N'-四甲基乙二胺(TMEDA)如(NMP)作为溶剂的还原剂和1-甲基-2-吡咯烷酮是必不可少的,得到所需的2,2-二氟乙酰基的化合物,和10种类型的以中等至优异的产率获得2,2-二氟链烷酸酯。相同的反应条件适用于炔烃的2,2-二氟乙酰化,以中等至优异的产率获得10种类型的2,2-二氟烯酸酯。
更新日期:2020-04-23
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