Abstract
Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.
Highlights
Hypervalent iodine chemistry has received considerable attention in recent years, in the area of small molecule synthesis [1,2,3]. Reasons for this include the ease-of-use of hypervalent iodine reagents, their low toxicity and the ability to effect useful, novel synthetic transformations
Iodonium salts are iodine(III) species with two carbon ligands and one non-carbon ligand [4]. These compounds are of increasing importance in synthesis, the majority of reported research in this area deals with the utility of diaryliodonium salts [5]
Alkenyl(aryl)iodonium salts are readily prepared from vinyl metal compounds, including silanes [8], stannanes [9], boronates/boronic acids [10], and zirconiums [11], by metal-iodine(III) exchange and from alkynyl(aryl)iodonium salts by conjugate addition of nucleophiles under protic conditions [12,13]
Summary
Hypervalent iodine chemistry has received considerable attention in recent years, in the area of small molecule synthesis [1,2,3]. Iodonium salts are iodine(III) species ( known as λ3 -iodanes) with two carbon ligands and one non-carbon ligand [4] These compounds are of increasing importance in synthesis, the majority of reported research in this area deals with the utility of diaryliodonium salts [5]. Hypervalent iodine reagents are known to undergo addition reactions to alkynes to generate alkenyl(aryl)iodonium salts [14,15]. These iodonium salts are reactive compounds due to the exquisite leaving group ability of the aryliodonium moiety coupled with its highly electron-withdrawing nature [16].
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