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.
Authors
- Ajay K. Sah (ORCID: https://orcid.org/0000-0001-7889-5447)
- Parmeshthi Parikh
- Krishnan Rangan (ORCID: https://orcid.org/0000-0002-0518-8431)
- Anuvasita Parikh
- Santosh Kumar Mishra (ORCID: https://orcid.org/0000-0001-8616-2606)
Institutions
- Birla Institute of Technology and Science - Hyderabad Campus (IN)
- Birla Institute of Technology and Science, Pilani (IN)
Publication Details
- 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
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Birla Institute of Technology and Science, Pilani