Ambient Temperature Dehydrogenative C(Ar)-H Carbonylative Lactamization of 2-Arylanilines Using DMF as C1-Source

Yong-Ze Chen; Ting-Hui Ding; Qiang-Qiang Li; Jian-Ping Qu; Yan-Biao Kang

doi:10.1021/acs.orglett.3c00585

Ambient Temperature Dehydrogenative C(Ar)-H Carbonylative Lactamization of 2-Arylanilines Using DMF as C1-Source

Org Lett. 2023 Apr 21;25(15):2611-2615. doi: 10.1021/acs.orglett.3c00585. Epub 2023 Apr 7.

Authors

Yong-Ze Chen¹, Ting-Hui Ding¹, Qiang-Qiang Li¹, Jian-Ping Qu², Yan-Biao Kang¹

Affiliations

¹ Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
² Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

PMID: 37027142
DOI: 10.1021/acs.orglett.3c00585

Abstract

The direct dehydrogenative C-H cleaving carbonylative lactamization of 2-arylanilines promoted by visible light and potassium bases is reported. Solvent DMF acts as the sole carbonyl source in the absence of an oxidant. The irreversible release of hydrogen gas drags this reaction to the stable phenanthridinone products. This work provides a direct conversion of a broad range of 2-arylanilines to various phenanthridinones. This method could be applied in the synthesis of bioactive molecules and organic optoelectronic materials.