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Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement
Journal article   Peer reviewed

Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement

Ever A. Blé-González, Stephen R. Isbel, Olatunji S. Ojo, Patrick C. Hillesheim, Matthias Zeller and Alejandro Bugarin
New journal of chemistry
2023

Abstract

Sulfones are fascinating and highly used functional groups, but current syntheses still have limitations. Here, a regiodivergent transition metal-free approach towards sulfones [( E )-allylic sulfones and α-sulfonylmethyl styrenes] is reported. The method employs commercially available olefins, bases, additives, solvents, and sodium sulfinates (RSO 2 Na) and produces adducts in good yields. Considering that up to 4 reactions (bromination, dearomative rearrangement, E2, and S N 2) are happening, this approach is very efficient. The structures of key adducts were confirmed by X-ray crystallography.
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