Issue 39, 2023

Pd@GO catalyzed stereo- and regio-selective addition of arenes to alkynes and synthesis of coumarins via C–H functionalization

Abstract

A stereo- and regio-selective addition of arenes to alkynes via C–H bond functionalization has been developed using palladium nanoparticles supported on graphite oxide (Pd@GO) as the reusable catalyst. The prepared catalyst was characterized by various spectroscopic techniques such as FT-IR, TEM, SEM, EDX, P-XRD, and XPS analysis. The thermal stability of the catalyst was established by TGA. The C–H functionalized products were obtained in good to excellent yields (69–92%) at room temperature. The methodology further extended to the synthesis of biologically and pharmaceutically important coumarin molecules from phenols and alkynes. Good to excellent yields of the coumarins (74–92%) were obtained. After the reaction, the catalyst was separated by centrifugation followed by filtration. The recovered catalyst was washed and reused up to five cycles. The advantages of this method are the simple procedure of the catalyst preparation, high catalytic efficiency, high selectivity, good functional group tolerance, low catalyst loading, and gram-scale synthesis.

Graphical abstract: Pd@GO catalyzed stereo- and regio-selective addition of arenes to alkynes and synthesis of coumarins via C–H functionalization

Supplementary files

Article information

Article type
Paper
Submitted
05 Aug 2023
Accepted
21 Sep 2023
First published
22 Sep 2023

Org. Biomol. Chem., 2023,21, 7928-7934

Pd@GO catalyzed stereo- and regio-selective addition of arenes to alkynes and synthesis of coumarins via C–H functionalization

L. Kyndiah, F. K. Sarkar, S. Gajurel, R. Sarkar, J. M. H. Anal and A. K. Pal, Org. Biomol. Chem., 2023, 21, 7928 DOI: 10.1039/D3OB01237A

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