Synthesis of aryl sulfonium salts from aryl nitro compounds

Positron emission tomography (PET) scans serve as a useful tool in medicine and science for detection of changes in cellular systems as well as tracing of functions within a biological system. PET scans often use fluorine-18 as a medium for detection. but fluorine-18 must be introduced to a system as a component of a larger compound (Sander, et al ..2015),.
Incorporation of fluorine-18 into aromatic compounds is generally accomplished by nucleophilic aromatic substitution reactions. These reactions may employ halides, nitro groups, iodonium salts, stannanes, or sulfonium salts as leaving groups, since high radiolabellng yields are desirable for PET tracers.
Diaryl thioethers with novel functional groups will be synthesized from inexpensive and stable nitroaryl compounds (Scheme 1 ).
Nitro aryl compounds containing ketones. phenols, aikyls, ethers, and nitriles have been reacted by this method to synthesize diaryl thioethers (Bahekar, et al.,2013).
However, esters, aldehydes, and combinations of multiple functional groups have yet to be tested. Thioether compounds (Table 1) are to be converted to sulfonium salts through literature procedures.
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Abstract/Description: Positron emission tomography (PET) scans serve as a useful tool in medicine and science for detection of changes in cellular systems as well as tracing of functions within a biological system. PET scans often use fluorine-18 as a medium for detection. but fluorine-18 must be introduced to a system as a component of a larger compound (Sander, et al ..2015),. Incorporation of fluorine-18 into aromatic compounds is generally accomplished by nucleophilic aromatic substitution reactions. These reactions may employ halides, nitro groups, iodonium salts, stannanes, or sulfonium salts as leaving groups, since high radiolabellng yields are desirable for PET tracers. Diaryl thioethers with novel functional groups will be synthesized from inexpensive and stable nitroaryl compounds (Scheme 1 ). Nitro aryl compounds containing ketones. phenols, aikyls, ethers, and nitriles have been reacted by this method to synthesize diaryl thioethers (Bahekar, et al.,2013). However, esters, aldehydes, and combinations of multiple functional groups have yet to be tested. Thioether compounds (Table 1) are to be converted to sulfonium salts through literature procedures.
Subject(s): Flash chromatography
Undergraduate Research
Synthesis
Diaryl thioethers
PET scans