A useful aminohalogenation reaction for the cyclization of O-alkynyl carbamates under copper catalysis has been developed. N-Halosuccinimides have been used as a halogen source. The intramolecular C-N bond formation occurs selectively affording haloalkylidene substituted heterocycles. Just in the case of alpha,alpha-cyclohexyl-substituted propargyl carbamate, the alkoxyhalogenation pathway was operative. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level. Keywords

Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates / S. Giofre', C. Loro, L. Molteni, C. Castellano, A. Contini, D. Nava, G. Broggini, E.M. Beccalli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2021:11(2021 Mar 19), pp. 1750-1757. [10.1002/ejoc.202100202]

Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

Giofre', Sabrina;Molteni, Letizia;Castellano, Carlo;Contini, Alessandro;Nava, Donatella;Beccalli, Egle Maria
2021-03-19

Abstract

A useful aminohalogenation reaction for the cyclization of O-alkynyl carbamates under copper catalysis has been developed. N-Halosuccinimides have been used as a halogen source. The intramolecular C-N bond formation occurs selectively affording haloalkylidene substituted heterocycles. Just in the case of alpha,alpha-cyclohexyl-substituted propargyl carbamate, the alkoxyhalogenation pathway was operative. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level. Keywords
aminohalogenation, alkoxyhalogenation, copper catalysis, carbamates, DFT calculations, intramolecular reaction;
Settore CHIM/06 - Chimica Organica
26-feb-2021
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/819644
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