Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines.

Org Lett

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

Published: April 2022

A series of indole-derived alkenes have been designed and applied in a photocatalytic cascade reaction with bromodifluoroacetate esters, affording an unknown type of tetracyclic tetrahydro-γ-carboline derivative in up to 90% yields. Mechanistic studies suggest that the reaction proceeds with tetrahydro-γ-carboline as a key intermediate. The reaction tolerates a diverse pool of substrates, which provides an efficient method for the construction of tetracyclic tetrahydro-γ-carboline compounds.

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http://dx.doi.org/10.1021/acs.orglett.2c00626DOI Listing

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