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

Year: 2024

Type: article

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 (A3) coupling reaction under solvent‐free condition. The formation of aminal intermediate during the reaction has been confirmed by 1H‐NMR and single‐crystal X‐ray diffraction studies. The catalytic system is reusable without any appreciable loss in the enantioselectivity or product yield.

Source: ChemPlusChem

DOI: 10.1002/cplu.202400381

Authors: Santosh Kumar Mishra, Parmeshthi Parikh, Anuvasita Parikh, Krishnan Rangan, Ajay Kumar Sah

Institutions: Birla Institute of Technology and Science, Pilani, Birla Institute of Technology and Science - Hyderabad Campus

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Birla Institute of Technology and Science, Pilani

OpenAlex ID: W4401827133

FWCI: 0.282

Cites: 60

Cited by: 2

Related to: 10