Divergent upgrading pathways of sulfones with primary alcohols: nickel-catalyzed α-alkylation under N 2 and metal-free promoted β-olefination in open air.

We report here our findings on the diverse reaction results of sulfones and alcohols. In the presence of NiCl 2 /P( t -Bu) 3 and under a N 2 atmosphere, α- C -alkylation of sulfones with alcohols occurs through a borrowing-hydrogen mechanism; when the reaction was carried out in the open air without nickel, the product was not the predicted α,β-unsaturated sulfone, but the β-alkenyl sulfone, which is a useful building block in organic synthesis.