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

Authors

  • Никита А. Дриго M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Александр Н. Горбунов M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Дмитрий Н. Горбунов M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Марта Ю. Таланова M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Юлия С. Кардашева M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Владимир В. Ковалев M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Антон Л. Максимов M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991
  • Иван М. Вацуро M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

DOI:

https://doi.org/10.1007/3378

Keywords:

calixarenes, triazoles, click chemistry, hydroformylation, phosphines

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*

Author Biographies

Никита А. Дриго, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Никита Андреевич Дриго

Александр Н. Горбунов, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Александр Николаевич Горбунов

Дмитрий Н. Горбунов, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Дмитрий Николаевич Горбунов

Марта Ю. Таланова, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Марта Юрьевна Таланова

Юлия С. Кардашева, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Юлия Сергеевна Кардашева

Владимир В. Ковалев, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Владимир Васильевич Ковалев

Антон Л. Максимов, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Антон Львович Максимов

Иван М. Вацуро, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory , Moscow 119991

Иван Михайлович Вацуро

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Published

2016-12-29

Issue

Vol. 52 No. 12 (2016)

Section

Original Papers