- Highly atom-economic, catalyst- and solvent-free oxidation of sulfides into sulfones using 30% aqueous H2O2
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Highly atom-efficient oxidation of sulfides into sulfones under solvent- and catalyst-free reaction conditions using a 30% aqueous solution of H 2O2 at 75 °C is reported. A structurally diverse set of phenyl alkyl-, phenyl benzyl-, benzyl alkyl-, dialkyl-, heteroaryl alkyl- and cyclic sulfides were transformed into sulfones regardless of the aggregate state and electronic nature of the substituents. In spite of the heterogeneous reaction mixtures throughout the work, no difficulties with stirring and reaction progress were noted. In numerous cases, only 10 mol% excess of H 2O2 was used, thus contributing considerably to the high atom economy of the process. Some solid substrates required a variable excess of hydrogen peroxide; however, the reactions were performed strictly without organic solvents. The transformation was demonstrated to be amenable for scale-up with both liquid and solid sulfides. In addition, isolation and purification of the crude products can be simply done with only filtration and crystallization.
- Jereb, Marjan
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supporting information
p. 3047 - 3052,6
(2020/09/16)
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- Methanesulfonylation of deactivated aromatics with superelectrophilic CH3so2F·3SbF5 and (CH3so2)2O-2CF3so 3H/B(O3SCF3)3 systems
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Methanesulfonylation of various deactivated arenes, including tri- and tetrafluorobenzenes, was achieved in good yield under mild conditions using superelectrophilic CH3SO2F/3SbF5 and (CH3SO2O)2O/2CF3SO 3H-B(O3SCF3)3 reagent systems. 1998 MAHK "Hayka/Interperiodica".
- Olah,Orlinkov,Oxyzoglou,Prakash, G.K. Suria
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p. 1573 - 1578
(2007/10/03)
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- An alternative synthesis of chlorinated biphenyl methylsulfonyl metabolites
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Published methods of synthesizing chlorinated biphenyl methylsulfones require the separation of a complex mixture of impurities and isomers using both normal and reverse phase HPLC. Even with semi-preparative scale equipment, the process is tedious and time-consuming. In this report, the palladium-catalyzed addition of an aryl iodide to an aryl trimethylstannane has been exploited to produce these compounds in high purity (≥ 99%) using conventional techniques of purification. The reaction has been demonstrated for a group of methylsulfonyl CBs representing 0 to 3 ortho-chlorine interactions between the biphenyl rings and with the methylsulfonyl group at either the 3- or 4- position.
- Mortimer, Richard D.,Newsome, W. Harvey
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p. 935 - 946
(2007/10/03)
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