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Citation: YI Wen-Bin, CAI Chun. Friedel-Crafts Acylation in Fluorous Biphasic Systems Catalyzed by Rare Earth(Ⅲ) Perfluorooctanesulfonates[J]. Chinese Journal of Applied Chemistry, ;2005, 22(11): 1187-1191. shu

Friedel-Crafts Acylation in Fluorous Biphasic Systems Catalyzed by Rare Earth(Ⅲ) Perfluorooctanesulfonates

YI Wen-Bin ,
CAI Chun ^,

1.
Chemical Engineering College, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: CAI Chun,
Received Date: 29 December 2004
Available Online: 16 March 2005
Fund Project: 国防科工委"十五"预研基金资助项目(40406020103) (40406020103)

The catalysts of rare earth(Ⅲ) perfluorooctanesulfonates(RE(OSO₂C₈F₁₇)₃,RE=Sc,Y,La~Lu) had been prepared and Friedel-Crafts acylation anisole with Ac₂O on RE(OSO₂C₈F₁₇)₃ catalysts in fluorous biphasic systems were investigated.Perfluorohexane(C₆F₁₄),perfluoromethylcyclohexane(C₇F₁₄),perfluorotoluene(C₇F₈),perfluoro-octane(C₈F₁₈),perfluorooctyl bromide(C₈F₁₇Br) and perfluorodecalin(C₁₀F₁₈,cis and trans-mixture) can be used as fluorous solvents for this reaction.Effects of the ratio of fluorous phase/organic phase and different acylation agents on the reaction were studied.The results show that the reaction exhibits a high para-selectivity of the acylation;Y(OSO₂C₈F₁₇)₃ and C₁₀F₁₈ are the best catalyst and fluorous solvent respectively.The yield of Friedel-Crafts acylation of anisole with Ac₂O was 56% by using Y(OSO₂C₈F₁₇)₃ as the catalyst and C₁₀F₁₈ as the fluorous solvent,and para-selectivity exceeded 99%.By simple phase-separation,the catalytic activity showed a small drop after the fluorous phase containing only the catalyst was re-utilized for five times.
- fluorous biphasic catalysis,
- rare earth(Ⅲ) perfluorooctanesulfonate,
- perfluorocarbons,
- Friedel-Crafts acylation
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