Abstract
The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.
Highlights
From a synthetic perspective, sulfones are versatile intermediates[4] and are implicit in such classic transformations as the Ramberg−Backlund reaction[5] and the Julia olefination.[6]
Metal sulfinates can be formed by treating an organometallic reagent with sulfur dioxide gas,[11] but this protocol is unattractive due to the difficulties in handling a toxic gaseous reagent.[12]
The complex formed between DABCO and sulfur dioxide, DABSO, was first employed by us in a novel palladium-catalyzed aminosulfonylation reaction[13] and subsequently in a streamlined version of Barrett’s sulfonamide synthesis.[14]
Summary
Sulfones are versatile intermediates[4] and are implicit in such classic transformations as the Ramberg−Backlund reaction[5] and the Julia olefination.[6]. The generation of metal sulfinates from organometallic reagents and DABSO was identified as a potentially efficient and versatile route into sulfone synthesis.
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