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Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-<i>jk</i>]carbazoles

Hang‐Dong Zuo, Xi Chen, Ya‐Yu Yuan, Yue Zhang, Jianwu Liu, Shenghu Yan, Wen‐Juan Hao, Bo Jiang

2024Organic Letters24 citationsDOI

Abstract

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1- jk ]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This photocatalytic approach exhibits a wide substrate compatibility and excellent tolerability toward various functional groups and boasts the benefit of efficient ring formation and chemical bond creation.

Topics & Concepts

Indole testChemistryPhotocatalysisCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-<i>jk</i>]carbazoles | Litcius