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Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates
Author(s) -
Giofrè Sabrina,
Loro Camilla,
Molteni Letizia,
Castellano Carlo,
Contini Alessandro,
Nava Donatella,
Broggini Gianluigi,
Beccalli Egle M.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100202
Subject(s) - chemistry , propargyl , intramolecular force , carbamate , catalysis , halogen , copper , medicinal chemistry , transition state , reaction mechanism , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
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.