European Journal of Organic Chemistry
European Journal of Organic Chemistry
5 years ago

Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors

Tomasz Mazurek, Tymoteusz Basak, Bartosz Górski, Michał Barbasiewicz, Dariusz Basiak, Alicja Talko
Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but mechanism of the fragmentation consists of four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce by-products, which are easily removed during workup. In our report we focused on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including type of the base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with mechanistic studies based on identification of intermediates and side products.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701766

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