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Synthesis 2025; 57(04): 754-763
DOI: 10.1055/s-0043-1773508
DOI: 10.1055/s-0043-1773508
paper
Recyclable Copper-Catalyzed Cascade Coupling/Condensation/ Deacylation Reaction of 2′-Halotrifluoroacetanilides with β-Keto Esters toward 2-(Trifluoromethyl)indoles
Authors
We thank the National Natural Science Foundation of China (No. 21664008) and Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education (No. KFSEMC-202206) for financial support.
Abstract
An efficient heterogeneous copper-catalyzed cascade coupling/condensation/deacylation reaction of 2′-halotrifluoroacetanilides with β-keto esters has been developed. The reaction proceeds smoothly in anhydrous dimethyl sulfoxide at 80–90 °C using Cs2CO3 as base and 10–20 mol% SBA-15-immobilized l-proline–CuI complex [SBA-15–l-Proline–CuI] as catalyst and provides a general and practical method for the assembly of a variety of polysubstituted 2-(trifluoromethyl)indoles in good to high yields. This heterogenized copper catalyst can be easily recovered via a simple centrifugation process and reused more than seven cycles with almost consistent catalytic activity.
Key words
copper - C–C coupling - 2-(trifluoromethyl)indoles - β-keto esters - heterogeneous catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773508.
- Supporting Information (PDF)
Publication History
Received: 15 September 2024
Accepted after revision: 03 December 2024
Article published online:
10 January 2025
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