Issue 1, 2014

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Aug 2013
Accepted
03 Oct 2013
First published
22 Oct 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 222-228

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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