Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides.

A domino difunctionalization of sulfonyl(acryl)imides to form β-substituted α-aryl amides is reported. This transformation involves a 1,4-addition followed by a polar Truce-Smiles rearrangement process, entropically driven by release of SO 2 . A wide range of carbon- and heteroatom-based nucleophiles and sulfonyl imides were employed, allowing rapid access to highly functionalized amides. In contrast to related reactions with a radical pathway, unbiased substrates could be employed. Despite the usual requirement of an electron-poor migrating moiety for the S N Ar event, we herein report unique and unprecedented vinylogous migrations of electron-neutral arenes. Additionally, a one-pot process toward β-amido amides starting from acrylic acids has been developed.