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Hydrogen-Bond-Promoted Metal-Free Hydroamination of Alkynes

Janet Bahri, Nour Tanbouza, Thierry Ollevier*, Marc Taillefer*, Florian Monnier*

*École Nationale Supérieure de Chimie de Montpellier, 34296 Montpellier, France; Université Laval, Québec, QC, G1V 0A6, Canada, Email: marc.tailleferenscm.fr, thierry.ollevierchm.ulaval.ca, florian.monnierenscm.fr

J. Bahri, N. Tanbouza, T. Ollevier, M. Taillefer, F. Monnier, Synthesis, 2019, 51, 2086-2090.

DOI: 10.1055/s-0039-1690988 (free Supporting Information)


Abstract

A metal-free regio- and stereoselective intermolecular hydroamination of arylacetylenes with aliphatic secondary amines provides various (E)-enamines in the presence of ethylene glycol as a solvent. The solvent plays a major role through hydrogen bonding and proton exchange.

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Key Words

hydroamination, alkynes, amines, metal-free, enamines, green chemistry


ID: J66-Y2019