Abstract
A new, simplified method for the synthesis of dimethyl aryl acylsulfonium salts has been developed. A series of dimethyl aryl acylsulfonium bromides were prepared by the reaction of aryl methyl ketones with hydrobromic acid and dimethylsulfoxide (DMSO). This sulfonium salt confirms that bromine production and the bromination reaction take place in the DMSO-HBr oxidation system. What’s more, it is also a key intermediate for the synthesis of arylglyoxals.
Highlights
In 1957, Kornblum first reported oxidation of α-bromoketones into α-ketoaldehydes by dimethylsulfoxide (DMSO) [1]
The DMSO-hydrobromic acid (HBr) system has been proved to be extremely efficient for the oxidation of the α-methyl group of arylketones [8]
When we tried to prepare arylglyoxals 2 from aryl methyl ketones 1 with the DMSO-HBr oxidation system in a sealed flask, we observed that aryl acylsulfonium bromides 3 were unexpectedly produced (Scheme 1)
Summary
In 1957, Kornblum first reported oxidation of α-bromoketones into α-ketoaldehydes by dimethylsulfoxide (DMSO) [1]. 1,2,3-trione derivatives in a DMSO-HBr system [2] This method has been modified by Folyd and applied to the preparation of aryldiketone (arylglyoxal) derivatives from arylmethyl ketones in high yield [3]. When we tried to prepare arylglyoxals 2 from aryl methyl ketones 1 with the DMSO-HBr oxidation system in a sealed flask, we observed that aryl acylsulfonium bromides 3 were unexpectedly produced (Scheme 1). We report a new and efficient route to aryl acylsulfonium salts and α-bromoacylsulfonium salts from aryl methyl ketones using the DMSO-HBr oxidation system. Sulfonium salts 3 have never been reported as key intermediate products in DMSO-HBr oxidations of arylmethyl ketones. Sulfonium salt 3 provides a new basis and reference mechanism for the oxidation of methyl ketones in DMSO-HBr system
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