Visible-Light-Induced Oxidation/[3 + 2] Cycloaddition/Oxidative Aromatization to Construct Benzo[ a]carbazoles from 1,2,3,4-Tetrahydronaphthalene and Arylhydrazine Hydrochlorides

Jiaxuan Shen; Nannan Li; Yanjiang Yu; Chunhua Ma

doi:10.1021/acs.orglett.9b02939

Visible-Light-Induced Oxidation/[3 + 2] Cycloaddition/Oxidative Aromatization to Construct Benzo[ a]carbazoles from 1,2,3,4-Tetrahydronaphthalene and Arylhydrazine Hydrochlorides

Org Lett. 2019 Sep 6;21(17):7179-7183. doi: 10.1021/acs.orglett.9b02939. Epub 2019 Aug 28.

Authors

Jiaxuan Shen¹, Nannan Li¹, Yanjiang Yu¹, Chunhua Ma¹

Affiliation

¹ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

PMID: 31456407
DOI: 10.1021/acs.orglett.9b02939

Abstract

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp³)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.