Generation of (nonafluoro-tert-butoxy)methyl ponytails for enhanced fluorous partition of aromatics and heterocycles

Abstract

The reaction of sodium perfluoro-tert-butoxide with benzylic carbon-bromide bond(s) leads to the formation of (nonafluoro-tert-butoxy)methyl ponytail(s), which can enhance the fluorous solubility and partition of aromatics and heterocycles.

Perfluorocarbons in Chemical Biology

“…We note that while trifluoromethyl groups do not strictly fall under the definition of perfluorocarbons, multiple CF 3 groups on one structure can often convey similar properties to a single, longer perfluoroalkyl chain. [32][33][34][35] Other fluorinated compounds, such as those containing single fluorine atoms or sp 2 CÀ F bonds, also have intriguing properties, which have been described elsewhere. [36][37][38]…”

New frontiers and developing applications in 19F NMR

“…1). A tris trifluoromethyl (t-butyl) group was recently developed and used to investigate nucleic acid conformation [120] and so-called (nonafluoro- tert -butoxy)methyl ponytails are generating increased attention [121]. Twelve equivalent fluorines were used by Takaoka et al .…”

Highly efficient synthesis of polyfluorinated dendrons suitable for click chemistry

“…3 However, most nuclei are unt for MRI applications, because of their inherent physical, chemical and biological properties. But 19 F has been shown to be exceptionally suitable for MRI as it is the second most sensitive, stable nucleus for MR spectroscopy (directly aer 1 H) and has 100% natural abundance. 4,5 Furthermore, the resonance frequency of 19 F differs by only 6% from the frequency of 1 H, which allows creating 19 F MR images on common 1 H MRI devices.…”

“…But 19 F has been shown to be exceptionally suitable for MRI as it is the second most sensitive, stable nucleus for MR spectroscopy (directly aer 1 H) and has 100% natural abundance. 4,5 Furthermore, the resonance frequency of 19 F differs by only 6% from the frequency of 1 H, which allows creating 19 F MR images on common 1 H MRI devices. 3 The conventional 1 H MRI makes use of the nuclear spin of the ubiquitous water molecules within organic tissues to enable visualization.…”

“…On the contrary, uorine is virtually absent in the biosphere. 5 The external addition of a suitable, uorinated compound (called probe or tracer) is thus mandatory for 19 F MRI. 6 Only teeth and the bone matrix contain considerable amounts of endogenous uorine.…”