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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
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
Publication History
Received: 15 September 2024
Accepted after revision: 03 December 2024
Article published online:
10 January 2025
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