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Zinc (II) Chloride as Phase Transfer Catalyst and as Catalyst of Cycloaddition Azide Ion to Heterocumulenes and Terminal Alkynes in Organic Solvents
Author(s) -
Vorona Svetlana V.,
Zevatskii Yuri E.,
Myznikov Leonid V.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903162
Subject(s) - cycloaddition , azide , chemistry , zinc , catalysis , nucleophile , chloride , sodium azide , photochemistry , organic chemistry
The system of NaN 3 –ZnCl 2 in organic solvents is effective for azide ion cycloaddition to heterocumulenes and terminal alkynes. The reaction proceeds readily in the case of heterocumulenes, so these transformations fall into the category of click reactions. The study on the reaction mechanism showed that role of zinc salt consists in transferring azide ion to the organic phase and decreasing the energy barrier of nucleophilic addition of azide ion to the unsaturated substrate.