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.

Acid-Mediated Decarboxylative C–H Coupling between Arenes and O-Allyl Carbamates / G. Broggini, C. Loro, J. Oble, F. Foschi, M. Papis, E.M. Beccalli, S. Giofrè, G. Poli. - In: ORGANIC CHEMISTRY FRONTIERS. - ISSN 2052-4129. - (2022). [Epub ahead of print] [10.1039/D2QO00114D]

Acid-Mediated Decarboxylative C–H Coupling between Arenes and O-Allyl Carbamates

E.M. Beccalli;
2022

Abstract

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.
Settore CHIM/06 - Chimica Organica
2022
8-feb-2022
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/904468
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