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Hypervalent Iodine‐Mediated Synthesis of Sulfones Using Organozinc Pivalates and Sulfinate Salts

Cunha, José C.; G. Rocha, Gabriel; Santos, Fábio M. F.; Bräse, Stefan ORCID iD icon 1; B. Marques, M. Manuel
1 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)

Abstract:

Sulfones are key motifs in pharmaceuticals, agrochemicals, and functional materials, as well as versatile intermediates in synthesis. We report a general and practical protocol for sulfone synthesis that combines the group-transfer capability of hypervalent iodine reagents (HIRs)—particularly in situ-generated sulfonyl-containing HIRs—with organozinc pivalates. The method delivers a broad range of sulfones in high yields under mild conditions, exhibiting excellent functional group tolerance. Importantly, the method enables efficient sulfonylation using sodium bicyclo[1.1.1]pentane sulfinate (BCP–SO2Na), providing streamlined access to functionalized BCP-sulfones. The protocol further enables in situ sulfinate generation and one-pot transformations. These findings expand the scope of HIR-enabled umpolung reactivity and offer a practical, modular and operationally simple platform for accessing sulfones with broad synthetic and medicinally relevance.


Verlagsausgabe §
DOI: 10.5445/IR/1000191448
Veröffentlicht am 24.03.2026
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 13.04.2026
Sprache Englisch
Identifikator ISSN: 1434-193X, 0075-4617, 0170-2041, 0365-5490, 0947-3440, 1099-0690, 1434-243X
KITopen-ID: 1000191448
Erschienen in European Journal of Organic Chemistry
Verlag John Wiley and Sons
Band 29
Heft 13
Seiten e202501113
Vorab online veröffentlicht am 01.03.2026
Nachgewiesen in OpenAlex
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