Issue 10, 2019

Highly regioselective and sustainable solar click reaction: a new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide–alkyne cycloaddition reaction

Abstract

The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(II) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.

Graphical abstract: Highly regioselective and sustainable solar click reaction: a new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide–alkyne cycloaddition reaction

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2019
Accepted
04 Apr 2019
First published
05 Apr 2019

Green Chem., 2019,21, 2677-2685

Highly regioselective and sustainable solar click reaction: a new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide–alkyne cycloaddition reaction

D. Yadav, N. Singh, T. W. Kim, J. Y. Kim, N. Park and J. Baeg, Green Chem., 2019, 21, 2677 DOI: 10.1039/C9GC00894B

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