DAST and Deoxofluor Mediated Nucleophilic Fluorination Reactions of Organic Compounds
Pp. 291-326 (36)
Rajendra P. Singha, Dayal T. Meshria and Jean’ne M. Shreeve
Organofluorine compounds have had a marked impact on medicinal and
agrochemical fields and the number of applications continues to grow. These
significant contributions arise from the unique changes that occur in the physical
and chemical properties of ordinary organic compounds wrought by the presence
of fluorine or a fluorine-containing group. Among a large number of methods
available to introduce fluorine into organic compounds, the nucleophilic
replacement of oxygen with fluorine is one of the most practical ways. Although
there are numerous fluorinating reagents available, diethylaminosulfur trifluoride
(DAST) and bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor) often are the
reagents of choice. Organic compounds containing oxygen in hydroxyl and
carbonyl groups are readily converted into their corresponding fluorinated
analogues by the introduction of one or two fluorine atoms, respectively, through
the use of these reagents. In some cases, depending upon the compound and the
reaction conditions, a very useful nonfluorinated product can also be produced.
Our interest in applying various synthetic methods to incorporate fluorine or a
fluorinated group into a large variety of organic compounds encouraged us to
summarize the recent chemistry of DAST and Deoxofluor.
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