Glucoconjugated Dinuclear Copper(II) Complex: An Efficient Catalyst for Stereoselective Synthesis of Trisubstituted Propargylamines <i>via</i> Solvent‐free A<sup>3</sup> Coupling Reaction

Development of catalytic systems using nontoxic natural precursors is the need of the era, and along this line, we have synthesized a new D-glucose derived ligand (4,6-O-ethylidene-N-(2-hydroxy-4-(octyloxy)benzylidene)-β-D-glucopyranosylamine) and its dinuclear copper(II) complex. The molecular structure of the complex has been established by single-crystal X-ray diffraction studies and detailed noncovalent intermolecular interactions present in it have been explored by Hirshfeld surface analysis. Further, the complex has been used as a catalyst in the enantioselective (87-99 % ee) synthesis of propargylamines in good to excellent yield (82-95 %) via aldehyde-amines-alkynes (A<sup>3</sup>) coupling reaction under solvent-free condition. The formation of aminal intermediate during the reaction has been confirmed by <sup>1</sup>H-NMR and single-crystal X-ray diffraction studies. The catalytic system is reusable without any appreciable loss in the enantioselectivity or product yield.

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Journal
ChemPlusChem
Published
2024-08-23
DOI
https://doi.org/10.1002/cplu.202400381
Citations
2
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.50

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article

Glucoconjugated Dinuclear Copper(II) Complex: An Efficient Catalyst for Stereoselective Synthesis of Trisubstituted Propargylamines via Solvent‐free A3 Coupling Reaction

Ajay K. Sah, Parmeshthi Parikh, Krishnan Rangan, Anuvasita Parikh et al.
2 citations
ChemPlusChem
Carbohydrate Chemistry and Synthesis
0.50
article

Glucoconjugated Dinuclear Copper(II) Complex: An Efficient Catalyst for Stereoselective Synthesis of Trisubstituted Propargylamines via Solvent‐free A3 Coupling Reaction

Ajay K. Sah, Parmeshthi Parikh, Krishnan Rangan, Anuvasita Parikh, Santosh Kumar Mishra
article en
2 citations

Abstract

Development of catalytic systems using nontoxic natural precursors is the need of the era, and along this line, we have synthesized a new D-glucose derived ligand (4,6-O-ethylidene-N-(2-hydroxy-4-(octyloxy)benzylidene)-β-D-glucopyranosylamine) and its dinuclear copper(II) complex. The molecular structure of the complex has been established by single-crystal X-ray diffraction studies and detailed noncovalent intermolecular interactions present in it have been explored by Hirshfeld surface analysis. Further, the complex has been used as a catalyst in the enantioselective (87-99 % ee) synthesis of propargylamines in good to excellent yield (82-95 %) via aldehyde-amines-alkynes (A<sup>3</sup>) coupling reaction under solvent-free condition. The formation of aminal intermediate during the reaction has been confirmed by <sup>1</sup>H-NMR and single-crystal X-ray diffraction studies. The catalytic system is reusable without any appreciable loss in the enantioselectivity or product yield.

ChemPlusChemVol. 89(12)
Birla Institute of Technology and Science - Hyderabad Campus (IN), Birla Institute of Technology and Science, Pilani (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Birla Institute of Technology and Science, Pilani
Clean water and sanitation
Openalex Percentile: Top 40%
Carbohydrate Chemistry and Synthesis
0.50
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Glucoconjugated Dinuclear Copper(II) Complex: An Efficient Catalyst for Stereoselective Synthesis of Trisubstituted Propargylamines <i>via</i> Solvent‐free A<sup>3</sup> Coupling Reaction — Ajay K. Sah, Parmeshthi Parikh, et al. · ChemPlusChem (2024) | TGRS Research Map | TGRS