EMAIL THIS PAGE TO A FRIEND

The Journal of organic chemistry

Selective perfluoro- and polyfluoroarylation of Meldrum's acid.


PMID 25271542

Abstract

This work describes the facile and mono-selective per- and polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated α-phenyl acetic acid derivatives, which provide straightforward access to fluorinated building blocks. The reaction takes place quickly, and most products were isolated without the need for chromatography. Importantly, this method provides an alternative strategy to access α-arylated Meldrum's acids, which avoids the need for aryl-Pb(IV) salts or diaryliodonium salts. Furthermore, we demonstrate the synthetic versatility and utility of the Meldrum's acid products by subjecting our products to several derivatizations of the Meldrum's acid products as well as photocatalytic hydrodefluorination.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

809195
3-(Perfluoropyridin-4-yl)-3-propyl-1,5-dioxaspiro[5.5]undecane-2,4-dione
C17H17F4NO4
809217
3-Methyl-3-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, ≥95%
C17H13F7O4
809292
3-Methyl-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undecane-2,4-dione
C15H13F4NO4
809071
3-Propyl-3-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione
C19H17F7O4
809136
3-Propyl-3-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione
C18H17F4NO6
809209
4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile
C19H17F4NO4
809179
N-Ethyl-N-isopropylpropan-2-aminium 3-(3-Chloro-2,5,6-trifluoropyridin-4-yl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate, ≥95%
C22H30ClF3N2O4
809160
N-Ethyl-N-isopropylpropan-2-aminium 3-(4-Acetyl-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate
C25H33F4NO5
809306
N-Ethyl-N-isopropylpropan-2-aminium 3-(4-Cyano-2,3,5,6-tetrafluorophenyl)-4-oxo-1,5-dioxaspiro[5.5]-undec-2-en-2-olate
C24H30F4N2O4
809225
N-Ethyl-N-isopropylpropan-2-aminium 4-Oxo-3-(2,3,5,6-tetrafluoro-4-(methoxycarbonyl)phenyl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate, ≥95%
C25H33F4NO6
809268
N-Ethyl-N-isopropylpropan-2-aminium 4-Oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate, ≥95%
C22H30F4N2O4