Ultra-fast Cu-based A3-coupling catalysts: faceted Cu2O microcrystals as efficient catalyst-delivery systems in batch and flow conditions
- 1 March 2022
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 100 (3), 217-223
- https://doi.org/10.1139/cjc-2021-0197
Abstract
Cu(I) catalysts were studied for the synthesis of a propargylamine via A3-coupling of aldehyde, amine, and alkyne, under solvent-free and low loading conditions, using batch microwave or flow thermal heating. We explore ultra-low loading conditions with Cu(I) salts as ultra fast and active catalysts featuring TOFs above 105 h-1. Well-defined octahedral and cubic Cu2O microcrystals were also successfully applied and compared to this reaction. Both types of microcrystals exhibited excellent catalytic activities within minutes, via in-situ generation of low dose of Cu(I) ions within the reaction medium, to achieve TON beyond 2000 and recycling up to 10 times in a flow reactor. The study of the catalytic system demonstrated that the activity was surface-structure dependent and allowed for the design of low Cu contamination A3-coupling systems, affording a product at the decigram scale, with Cu contamination below FDA recommendations for drug synthesis, without the need for a purification procedure.Keywords
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