Cascade Functionalization of C(sp3)-Br/C(sp2)-H Bonds: Access to Fused Benzo[ e]isoindole-1,3,5-trione via Visible-Light-Induced Reductive Radical Relay Strategy

Jia-Nan Zhu; Wen-Kang Wang; Yuan Zhu; Yin-Qiu Hu; Sheng-Yin Zhao

doi:10.1021/acs.orglett.9b02153

Cascade Functionalization of C(sp³)-Br/C(sp²)-H Bonds: Access to Fused Benzo[ e]isoindole-1,3,5-trione via Visible-Light-Induced Reductive Radical Relay Strategy

Org Lett. 2019 Aug 16;21(16):6270-6274. doi: 10.1021/acs.orglett.9b02153. Epub 2019 Jul 26.

Authors

Jia-Nan Zhu¹, Wen-Kang Wang¹, Yuan Zhu¹, Yin-Qiu Hu¹, Sheng-Yin Zhao¹

Affiliation

¹ College of Chemistry, Chemical Engineering and Biotechnology , Donghua University , Shanghai 201620 , People's Republic of China.

PMID: 31348662
DOI: 10.1021/acs.orglett.9b02153

Abstract

A reductive radical relay strategy for the construction of fused benzo[e]isoindole-1,3,5-trione through a reaction of α-bromo ketones with maleimides in the presence of Ir(ppy)₃ under visible-light irradiation is described. The protocol employs very mild reaction conditions and offers satisfactory yields. Moreover, the reaction proceeds through a cascade C(sp³)-Br/C(sp²)-H functionalization, double C-C bond formation, and oxidative aromatization sequence.