Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2- d]benzodiazepine Derivatives

Guifang Lian; Jingyu Li; Ping Liu; Peipei Sun

doi:10.1021/acs.joc.9b00937

Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2- d]benzodiazepine Derivatives

J Org Chem. 2019 Jul 19;84(14):9322-9329. doi: 10.1021/acs.joc.9b00937. Epub 2019 Jul 1.

Authors

Guifang Lian¹, Jingyu Li¹, Ping Liu¹, Peipei Sun¹

Affiliation

¹ School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials , Nanjing Normal University , Nanjing 210023 , China.

PMID: 31257876
DOI: 10.1021/acs.joc.9b00937

Abstract

A new photoredox-catalyzed cascade reaction is described to access fluorinated pyrrolo[1,2-d]benzodiazepine derivatives under mild conditions. In this process, single electron transfer (SET) between the excited state photocatalyst fac-Ir(ppy)₃ and ethyl bromodifluoroacetate initiated the regioselective radical addition to a wide range of 2-(1H-pyrrol-1-yl) anilines or indol-substituted anilines, followed by another SET process and intramolecular amidation.