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Review
. 2019 Aug 27;25(48):11193-11213.
doi: 10.1002/chem.201902019. Epub 2019 Jul 12.

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small-Molecule Synthons

Barry M Trost  1 , Christopher A Kalnmals  1
Affiliations
Review

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small-Molecule Synthons

Barry M Trost et al. Chemistry. .

Abstract

Sulfones are flexible functional groups that can act as nucleophiles, electrophiles, or even radicals. Changing the reaction conditions can completely alter the reactivity of a sulfonyl group, and as a result, molecules bearing multiple sulfones are versatile building blocks. This Review highlights the unique ability of 1,1- and 1,2-bis(sulfones) to masquerade as a vast array of reactive synthons including methane polyanions, vinyl cations, and all-carbon dipoles that would be difficult or impossible to access directly.

Keywords: C1 building blocks; reactive intermediates; sulfur; synthetic methods; umpolung.

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References

    1. None
    1. B. M. Trost, Bull. Chem. Soc. Jpn. 1988, 61, 107-124;
    1. A. El-Awa, M. N. Noshi, X. Mollat du Jourdin, P. L. Fuchs, Chem. Rev. 2009, 109, 2315-2349.
    1. None
    1. For an excellent overview of the chemistry of sulfones, including their synthesis and reactivity, see S. Patai, Z. Rappoport, C. Stirling (Eds.) The Chemistry of Sulphones and Sulphoxides, John Wiley & Sons, Chichester, 1988;

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