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Issue 1, 2014
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One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

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Abstract

A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.

Graphical abstract: One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

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Publication details

The article was received on 20 Aug 2013, accepted on 03 Oct 2013 and first published on 22 Oct 2013


Article type: Edge Article
DOI: 10.1039/C3SC52332B
Citation: Chem. Sci., 2014,5, 222-228
  • Open access: Creative Commons BY license
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    One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

    C. S. Richards-Taylor, D. C. Blakemore and M. C. Willis, Chem. Sci., 2014, 5, 222
    DOI: 10.1039/C3SC52332B

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