Metal-Free Regioselective N²-Arylation of 1H-Tetrazoles with Diaryliodonium Salts

Raktim Abha Saikia, Anurag Dutta, Bipul Sarma and Ashim Jyoti Thakur*

*Department of Chemical Sciences, Tezpur University, Napaam, Tezpur 784028, India, Email: ashimtezu.ernet.in

R. A. Saikia, A. Dutta, B. Sarma, A. J. Takur, J. Org. Chem., 2022, 87, 9782-9796.

DOI: 10.1021/acs.joc.2c00848

---

see article for more reactions

Abstract

The use of diaryliodonium salts enables a simple, metal-free regioselective N²-arylation strategy for 5-substituted-1H-tetrazoles to provide 2-aryl-5-substituted-tetrazoles. Diaryliodonium salts with a wide range of both electron-rich and previously challenged electron-deficient aryl groups are applicable. A one-pot system achieves the synthesis of 2,5-diaryl-tetrazoles directly from nitriles.

see article for more examples

proposed mechanism

---

---

Key Words

2H-Tetrazoles, Arylation

---

ID: J42-Y2022