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SYNTHESIS OF POLYFUNCTIONAL PHOSPHORUS-CONTAINING CALIXARENES BY AZIDE CYCLOADDITION TO ALKYNES

Никита А. Дриго, Александр Н. Горбунов, Дмитрий Н. Горбунов, Марта Ю. Таланова, Юлия С. Кардашева, Владимир В. Ковалев, Антон Л. Максимов, Иван М. Вацуро
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Abstract


Mono- and dibromo derivatives of calix[4]arene were used for the first time in phosphorylation, alkylation, and azide-alkyne cycloaddition sequence in order to synthesize polyfunctional macrocycles containing phosphine oxide groups at the upper rim and 1,4-di­substituted triazole rings at the lower rim. The effect of reaction conditions onto the selectivity of the lower-rim alkylation of phosphorus-containing calixarenes and the ratio of spatial isomers in the exhaustively alkylated products was studied. The reduction of phosphine oxide groups and modification of functional groups in the triazole rings were used for the synthesis of bulky hydrophilic phosphine-containing ligands. The catalytic activity of in situ obtained rhodium complexes of phosphine-containing calixarenes was preliminarily studied by 1-octene hydroformylation in ethanol.

Authors: Nikita A. Drigo, Alexander N. Gorbunov, Dmitry N. Gorbunov, Marta Yu. Talanova, Yulia S. Kardasheva, Vladimir V. Kovalev, Anton L. Maximov, Ivan M. Vatsouro*


Keywords


calixarenes; triazoles; click chemistry; hydroformylation; phosphines

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