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The synthesis of fluorescent benzofuro[2,3-c]pyridines via palladium-catalyzed heteroaromatic C–H addition and sequential tandem cyclization

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Abstract

A Pd-catalyzed tandem reaction of 2-(cyanomethoxy)chalcones with thiophenes through direct C–H addition and sequential intramolecular conjugate addition/cyclization/aromatization provides a diverse range of 3-aryl-1-(thiophen-2-yl)benzofuro[2,3-c]pyridines. A representative product was assessed as a ratiometric fluorescent probe for Hg2+. This chemistry could also be applied to the synthesis of other fused ring systems.

Graphical abstract: The synthesis of fluorescent benzofuro[2,3-c]pyridines via palladium-catalyzed heteroaromatic C–H addition and sequential tandem cyclization

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Article information


Submitted
18 Dec 2019
Accepted
27 Jan 2020
First published
10 Feb 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

The synthesis of fluorescent benzofuro[2,3-c]pyridines via palladium-catalyzed heteroaromatic C–H addition and sequential tandem cyclization

W. Xiong, Z. Chen, Y. Shao, R. Li, K. Hu and J. Chen, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01491H

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