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34.6.1.2.1 Method 1: Fluorination of Alkylbenzenes with Cesium Fluoroxysulfate

DOI: 10.1055/sos-SD-034-00199

Sai Krishna Murthy, A.; Tardivel, R.; Grée, R.Science of Synthesis, (200534313.

The fluorination of mono-, di-, and trimethyl-substituted benzenes 84 is possible with cesium fluoroxysulfate in acetonitrile. In the case of monosubstituted benzenes, the highest conversions of starting material into fluoro-substituted products 85 and 86 are achieved when 0.5 M solutions of alkyl-substituted aromatic derivatives in acetonitrile are treated with a 60% molar excess of cesium fluoroxysulfate in the absence of oxygen. As shown in Table 1, side-chain fluoro functionalizations (e.g., to give 85) are predominant, if not the exclusive process (entries 15).[‌50‌] In most of the disubstituted methylbenzene derivatives the benzylic fluoro functionalization is also a predominant process on reaction with cesium fluoroxysulfate (entries 68). However, complex mixtures of regioisomers are obtained in the case of the trimethylbenzenes (entries 911).

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