DABSO-Based, Three-Component, One-Pot Sulfone Synthesis

Alex S. Deeming, Claire J. Russell, Alan J. Hennessy and Michael C. Willis*

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom, Email: michael.willischem.ox.ac.uk

A. S. Deeming, C. J. Russell, A. J. Henessy, M. C. Willis, Org. Lett., 2014, 16, 150-153.

DOI: 10.1021/ol403122a

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Abstract

The addition of Grignard reagents or organolithium reagents to the SO₂-surrogate DABSO generates a diverse set of metal sulfinates, which can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums to give sulfone products.

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One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence

D. C. Lenstra, V. Vedovato, E. F. Flegeau, J. Maydom, M. C. Willis, Org. Lett., 2016, 18, 2086-2089.

One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides

E. F. Flegeau, J. M. Harrison, M. C. Willis, Synlett, 2016, 27, 101-105.

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Key Words

alkyl sulfones, benzyl sulfones, aryl sulfones, allyl sulfones, microwave synthesis

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ID: J54-Y2014