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.

Copper(II)-Catalyzed Aminohalogenation of Alkynyl Carbamates

Loro C.;Molteni L.;Broggini G.;
2021-01-01

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 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.
2021
Copper; Cyclization; DFT calculation; Homogeneous catalysis; Intramolecular reactions
Giofre, S.; Loro, C.; Molteni, L.; Castellano, C.; Contini, A.; Nava, D.; Broggini, G.; Beccalli, E. M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2120704
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