Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding

Chemical Communications : Chem Comm
Christopher M Poteat, Vincent N G Lindsay

Abstract

The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.

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Citations

Jul 16, 2020·The Journal of Organic Chemistry·Kazuki MatsuoAkichika Itoh

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Methods Mentioned

BETA
NMR
X-ray

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