Methyl Gallate as the Framework for the Construction of Fluorous Building Blocks

Abstract

Methyl gallate was used as the framework for the construction of the building blocks 3–5 with three fluorous ponytails. Fluorous gallate 3 was prepared from methyl gallate in three different pathways. The first is based on perfluorohexyl iodide addition to the corresponding allylderivative 1 and reduction of C-I bond in adduct 2; other ways are based on direct O-alkylation of methyl gallate by 3-(perfluorohexyl)propyl triflate and 3-(perfluorohexyl)propyl iodide, respectively. Reduction of polyfluoroalkylated gallate 3 provided benzyl alcohol 4, which can be easily converted to corresponding benzyl bromide 5.

Keywords:

• Dendron
• fluorinated gallate
• fluorous building blocks
• methyl gallate
• polyfluoroalkylation

ACKNOWLEDGMENTS

The authors thank the Ministry of Education, Youth, and Sports of Czech Republic (Grants LC 512, KAN200200651, MSM 0021620806) and the Grant Agency of the Czech Republic (Grant No. 203/06/0786) for financial support of this project.