Acid-mediated decarboxylative C–H coupling between arenes and O-allyl carbamates. Issue 6 (16th February 2022)

• Record Type: Journal Article
• Authors: Loro, Camilla; Oble, Julie; Foschi, Francesca; Papis, Marta; Beccalli, Egle M.; Giofrè, Sabrina; Poli, Giovanni; Broggini, Gianluigi
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 6(2022)
• Page Start: 1711
• Page End: 1718
• Publication Date: 2022-02-16
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00114d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Treatment of O -allyl N -tosyl carbamates with arenes 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. 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 appreciation of 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.