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Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl propenones

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Abstract

New radical-triggered multi-component cyclizations of β-alkynyl propenones have been developed, leading to 50 examples of sulfonated 1-indenones with generally good yields and high levels of stereoselectivity. The oxidant-free azosulfonylation of β-alkynyl propenones with aryldiazonium salts and DABSO was realized under the neutral–redox conditions where TBHP enabled the direct selenosulfonylation of β-alkynyl propenones by combining sulfinic acids and diphenyl diselenide. This protocol features a broad substrate scope, high functional group tolerance and mild reaction conditions.

Graphical abstract: Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl propenones

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Publication details

The article was received on 05 Nov 2017, accepted on 25 Nov 2017 and first published on 27 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC08516H
Citation: Chem. Commun., 2018, Advance Article
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    Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl propenones

    Z. Shen, Y. Wu, C. He, L. He, W. Hao, A. Wang, S. Tu and B. Jiang, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC08516H

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