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Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

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Design, Synthesis of 5-(2-Methylbenzofuran)-2-aryl-2H-tetrazole Derivatives via Cross-Coupling of N-H Free Tetrazoles with Boronic Acids

https://doi.org/10.14233/ajchem.2023.28074
Govu Ramana
Department of Chemistry, Natural Products Laboratory, Osmania University-500007, India
https://orcid.org/0009-0009-7254-4270
Gutam Madhu
Department of Chemistry, Natural Products Laboratory, Osmania University-500007, India
https://orcid.org/0000-0003-2963-566X
Yerrabelli Jayaprakash Rao
Department of Chemistry, Natural Products Laboratory, Osmania University-500007, India
https://orcid.org/0000-0003-4387-8334
Chitneni Prasad Rao
Department of Chemistry, Natural Products Laboratory, Osmania University-500007, India
https://orcid.org/0000-0003-0062-9856

Corresponding Author(s) : Chitneni Prasad Rao

prasadraoou@yahoo.com

Asian Journal of Chemistry, Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

Abstract

Chemical intermediates derived from 1,3-dipolar cycloaddition reactions, such as 5-substituted 1H-tetrazole, are commonly utilized to synthesize 1,5-disubstituted tetrazoles. In this work, a highly effective and useful strategy for the synthesis of 5-(2-methylbenzofuran-3-yl)-2-phenyl-2H-tetrazoles using environmentally safe 1 atm. O2 as oxidizer is reported. Moreover, the N-H unbound tetrazoles and low hazardous boronic acids are directly coupled with the catalytic amount (5 mol%) of Cu2O to form C-N bond without any formation of the additives. The proposed method is simple for the Cu-catalyzed reactions, which require only mild conditions and green, atom-efficient chemistry for the regioselective synthesis of 2,5-disubstituted 2H-tetrazoles.

Keywords

Benzofuran 2,5-Disubstituted 2H-tetrazoles C-N bond Low toxic Regioselective
Ramana, G., Madhu, G., Rao, Y. J., & Rao, C. P. (2023). Design, Synthesis of 5-(2-Methylbenzofuran)-2-aryl-2H-tetrazole Derivatives via Cross-Coupling of N-H Free Tetrazoles with Boronic Acids. Asian Journal of Chemistry, 35(8), 2001–2006. https://doi.org/10.14233/ajchem.2023.28074
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