(Hetero)aryl-SVI Fluorides: Synthetic Development and Opportunities

Magre, Marc; Ni, Shengyang; Cornella, Josep

doi:10.1002/anie.202200904

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(Hetero)aryl-S^VI Fluorides: Synthetic Development and Opportunities

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Magre, Marc
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ni, Shengyang
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella, Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Magre, M., Ni, S., & Cornella, J. (2022). (Hetero)aryl-S^VI Fluorides: Synthetic Development and Opportunities. Angewandte Chemie International Edition. doi:10.1002/anie.202200904.

Cite as: https://hdl.handle.net/21.11116/0000-000A-7133-D

Abstract

(Hetero)arylsulfur compounds where the S atom is in the oxidation state VI represent a large percentage of the molecular functionalities present in organic chemistry. More specifically, (hetero)aryl-S^VI fluorides have recently received enormous attention because of their potential as chemical biology probes, as a result of their reactivity in a simple, modular, and efficient manner. Whereas the synthesis and application of the level 1 fluorination at S^VI atoms (sulfonyl and sulfonimidoyl fluorides) have been widely studied and reviewed, the synthetic strategies towards higher levels of fluorination (levels 2 to 5) are somewhat more limited. This Minireview evaluates and summarizes the progress in the synthesis of highly fluorinated aryl-S^VI compounds at all levels, discussing synthetic strategies, reactivity, the advantages and disadvantages of the synthetic procedures, the proposed mechanisms, and the potential upcoming opportunities.