Issue 18, 2021

Copper-catalyzed [3 + 2]/[3 + 2] carboannulation of dienynes and arylsulfonyl chlorides enabled by Smiles rearrangement: access to cyclopenta[a]indene-fused quinolinones

Abstract

On one hand, the construction of two fused five-membered carbocyclic rings remains an extremely challenging topic in organic synthesis. On the other hand, transition-metal-catalyzed dienyne cycloaddition reactions have become one of the most powerful methods for the construction of diverse cyclic frameworks. Nevertheless, these methods are limited to noble transition-meal catalysis and non-radical cycloaddition modes. Here, a radical Smiles rearrangement strategy for allowing an unprecedented [3 + 2]/[3 + 2] carboannulation of dienynes with arylsulfonyl chlorides using cheap copper catalysis is described. This cascade method represents a novel cycloaddition mode for dienyne chemistry, which occurs by the sequence of addition of arylsulfonyl radical to a dienyne, a Smiles rearrangement and radical annulation to access cyclopenta[a]indene-fused quinolinones with excellent diastereoselectivity.

Graphical abstract: Copper-catalyzed [3 + 2]/[3 + 2] carboannulation of dienynes and arylsulfonyl chlorides enabled by Smiles rearrangement: access to cyclopenta[a]indene-fused quinolinones

Supplementary files

Article information

Article type
Research Article
Submitted
04 mei 2021
Accepted
11 jul 2021
First published
13 jul 2021

Org. Chem. Front., 2021,8, 5092-5097

Copper-catalyzed [3 + 2]/[3 + 2] carboannulation of dienynes and arylsulfonyl chlorides enabled by Smiles rearrangement: access to cyclopenta[a]indene-fused quinolinones

L. Zhou, X. Liu, H. Lu, G. Deng, Y. Liang, Y. Yang and J. Li, Org. Chem. Front., 2021, 8, 5092 DOI: 10.1039/D1QO00703C

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