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Issue 20, 2019
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Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent–solvent halogen bonding

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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.

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

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Article information


Submitted
21 Jan 2019
Accepted
14 Feb 2019
First published
14 Feb 2019

Chem. Commun., 2019,55, 2912-2915
Article type
Communication

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

C. M. Poteat and V. N. G. Lindsay, Chem. Commun., 2019, 55, 2912 DOI: 10.1039/C9CC00550A

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