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

Haoqi ZhangYi XiaoMiran LemmererTommaso BortolatoNuno Maulide
Published in: JACS Au (2024)
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.
Keyphrases
  • magnetic resonance
  • molecular docking
  • magnetic resonance imaging
  • computed tomography
  • cancer therapy
  • ionic liquid
  • drug delivery
  • electron transfer
  • tandem mass spectrometry