I2 Catalyzed and TBHP/Ammonium-Promoted Conversion of Arylethanone to Nitriles via β-Scission of Iminyl Radicals

Kui Zheng; Chen Liang; Hailong Chen; Yang Zhao; Zhenlian Wang; Jiang Cheng

doi:10.1021/acs.orglett.4c01142

I₂ Catalyzed and TBHP/Ammonium-Promoted Conversion of Arylethanone to Nitriles via β-Scission of Iminyl Radicals

Org Lett. 2024 Apr 26. doi: 10.1021/acs.orglett.4c01142. Online ahead of print.

Authors

Kui Zheng¹, Chen Liang¹, Hailong Chen¹, Yang Zhao¹, Zhenlian Wang¹, Jiang Cheng^{1

2}

Affiliations

¹ College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China.
² Lab of Biohealth Materials and Chemistry of Wenzhou, Wenzhou University, Wenzhou 325035, P. R. China.

PMID: 38668726
DOI: 10.1021/acs.orglett.4c01142

Abstract

Herein, we report a general I₂-catalyzed and TBHP/ammonium-promoted conversion of arylethanone to aromatic nitriles under air. This procedure proceeded with the β-scission of iminyl radical, which was facilitated via quenching the released alkyl radical by tert-butyl peroxyl radical leading to peroxide followed with Kornblum-DeLaMare rearrangement. A series of aryl methyl ketone and alkyl aryl ketone worked well with good functional group tolerance in high yields. As such, this metal-free procedure represents a facile, safe, green, and practical procedure in conversion of arylethanone to aromatic nitriles.