Synthesis of Phenanthridines through Iodine-Supported Intramolecular C-H Amination and Oxidation under Visible Light

Yan Gao; Yi Jing; Lixin Li; Jie Zhang; Xuenian Chen; Yan-Na Ma

doi:10.1021/acs.joc.0c01390

Synthesis of Phenanthridines through Iodine-Supported Intramolecular C-H Amination and Oxidation under Visible Light

J Org Chem. 2020 Oct 2;85(19):12187-12198. doi: 10.1021/acs.joc.0c01390. Epub 2020 Sep 11.

Authors

Yan Gao¹, Yi Jing¹, Lixin Li², Jie Zhang¹, Xuenian Chen^{1

3}, Yan-Na Ma¹

Affiliations

¹ School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, Henan Normal University, Xinxiang, Henan 453007, China.
² College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang, Henan 464000, China.
³ College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan 450001, China.

PMID: 32872780
DOI: 10.1021/acs.joc.0c01390

Abstract

Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C-H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.