Decarboxylative Cross-Dehydrogenative Coupling of Tetrahydroisoquinoline and Alkynoic Acids Using Recyclable Carbon Nanotube Supported Copper/Nickel Oxide Catalysts

IF 3.8 3区化学 Q2 CHEMISTRY, PHYSICAL

ChemCatChem Pub Date : 2025-02-16 DOI:10.1002/cctc.202401821

Robin Prakash Sirvin Rajan, Ji Dang Kim, Hyun Chul Choi, Sunwoo Lee

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Abstract

We present a decarboxylative cross-dehydrogenative coupling (CDC) reaction between tetrahydroisoquinoline (THIQ) derivatives and alkynoic acids using a carbon nanotube-supported copper/nickel oxide (CNT-CuO/Ni) catalyst. This catalyst leverages the catalytic properties of copper and magnetic recoverability of nickel to facilitate efficient carbon─carbon bond formation under mild conditions while allowing for easy separation and reuse. Under optimized conditions, the reaction produced various 1-alkynyl-2-aryl-1,2,3,4-tetrahydroisoquinoline derivatives in good yields. The CNT-CuO/Ni catalyst exhibited significant reusability, retaining high catalytic performance through 12 reaction cycles. Competition experiments revealed that the electronic properties of substituents on the phenyl propiolic acid and THIQ aryl groups had a minimal effect on the reaction outcome. This study underscores the potential of CNT-CuO/Ni as a recyclable catalyst for sustainable organic synthesis in decarboxylative CDC reactions.

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来源期刊

ChemCatChem 化学-物理化学

CiteScore

8.10

自引率

4.40%

发文量

511

审稿时长

1.3 months

期刊介绍： With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.