Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

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 ca...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-03, Vol.2021 (11), p.1750-1757
Main Authors: Giofrè, Sabrina, Loro, Camilla, Molteni, Letizia, Castellano, Carlo, Contini, Alessandro, Nava, Donatella, Broggini, Gianluigi, Beccalli, Egle M.
Format: Article
Language:English
Subjects:
Carbamates (tradename)
Copper
Copper compounds
Cyclization
DFT calculation
Homogeneous catalysis
Intramolecular reactions
Substitutes
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Summary: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 α,α‐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. The aminohalogenation reaction of O‐alkynyl carbamates under copper catalysis has been developed. The intramolecular C−N bond formation occurs selectively affording haloalkylidene substituted heterocycles. In the case of α,α‐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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100202