Transition-Metal Catalyst Free Oxidative Radical Arylation of N-Methylpyrrole

Esma Kocaoğlu; Muhammed A Karaman; Hatun Tokgöz; Oktay Talaz

doi:10.1021/acsomega.7b00988

Transition-Metal Catalyst Free Oxidative Radical Arylation of N-Methylpyrrole

ACS Omega. 2017 Aug 28;2(8):5000-5004. doi: 10.1021/acsomega.7b00988. eCollection 2017 Aug 31.

Authors

Esma Kocaoğlu¹, Muhammed A Karaman¹, Hatun Tokgöz¹, Oktay Talaz¹

Affiliation

¹ Department of Chemistry, Kamil Özdağ Science Faculty, Karamanoğlu Mehmetbey University, 70100 Karaman, Turkey.

Abstract

This study represents an expansion of the application of catalysis in air through conventional coupling and free radical processes. A reactive free aryl radical intermediate was generated via the oxidation of an activated Ar-NH-NH₂ bond by air as a simple and readily available oxidant. For this purpose, the usability of phenylhydrazine and phenylhydrazine hydrochloride salt reagents for the direct arylation of pyrrole with aryl radicals was investigated. The facile coupling of N-methylpyrrole with aryl radicals was easily applied for the convenient direct synthesis of C-2 arylated pyrroles without a transition-metal catalyst.