Article Dans Une Revue Organic Chemistry Frontiers Année : 2022

Acid-mediated decarboxylative C–H coupling between arenes and O -allyl carbamates

Camilla Loro
Francesca Foschi
Marta Papis
Egle Beccalli
Sabrina Giofrè
  • Fonction : Auteur

Résumé

Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)2 or TMSOTf as promoters, affords N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter and of the aryl substrates. A full mechanistic rational allowing to appreciate the outcome of these novel C–H based cascades is proposed. An initial acid promoted decarboxylative / deamidative Friedel-Crafts allylation takes place. After protonation of the allylated arene, evolution of the resulting cation may follow different paths depending on the nature of the arene partner and of the allyl moiety in the carbamate

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hal-03783470 , version 1 (22-09-2022)

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Camilla Loro, Julie Oble, Francesca Foschi, Marta Papis, Egle Beccalli, et al.. Acid-mediated decarboxylative C–H coupling between arenes and O -allyl carbamates. Organic Chemistry Frontiers, 2022, 9 (6), pp.1711-1718. ⟨10.1039/d2qo00114d⟩. ⟨hal-03783470⟩
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