The catalytic activity of carbon-supported Cu(I)-phosphine complexes for the microwave-assisted synthesis of 1,2,3-triazoles

Ivy L. Librando, Abdallah G. Mahmoud, Sónia A. C. Carabineiro, M. Fátima C. Guedes Da Silva, Carlos F. G. C. Geraldes, Armando J. L. Pombeiro

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1 Citation (Scopus)
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Abstract

A set of Cu(I) complexes with 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo-[3.3.1]nonane (DAPTA) phosphine ligands viz. [CuX(κP-DAPTA)3] (1: X = Br; 2: X = I) and [Cu(µ-X)((κP-DAPTA)2]2 (3: X = Br; 4: X = I) were immobilized on activated carbon (AC) and multi-walled carbon nanotubes (CNT), as well as on these materials after surface functionalization. The immobilized copper(I) complexes have shown favorable catalytic activity for the one-pot, microwave-assisted synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition reaction (CuAAC). The heterogenized systems with a copper loading of only 1.5-1.6% (w/w relative to carbon), established quantitative conversions after 15 min, at 80 °C, using 0.5 mol% of catalyst loading (relative to benzyl bromide). The most efficient supports concerning heterogenization were CNT treated with nitric acid and NaOH, and involving complexes 2 and 4 (in the same order, 2_CNT-ox-Na and 4_CNT-ox-Na). The immobilized catalysts can be recovered and recycled by simple workup and reused up to four consecutive cycles although with loss of activity.

Original languageEnglish
Article number185
Pages (from-to)1-15
Number of pages15
JournalCatalysts
Volume11
Issue number2
DOIs
Publication statusPublished - Feb 2021

Keywords

  • Carbon nanotubes
  • Click chemistry
  • Cu(I) complexes
  • CuAAC
  • DAPTA ligands
  • Microwave
  • Phosphine
  • Triazoles

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