Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 11, Pages 1750-1757Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100202
Keywords
Copper; Cyclization; DFT calculation; Homogeneous catalysis; Intramolecular reactions
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A useful aminohalogenation reaction for the cyclization of O-alkynyl carbamates under copper catalysis has been developed in this study. N-Halosuccinimides were used as the halogen source, leading to selective intramolecular C-N bond formation and the generation of haloalkylidene substituted heterocycles. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level.
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.
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