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Palladium-catalyzed site-selective direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[d]isoxazoles

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Abstract

A palladium-catalyzed direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[d]isoxazoles has been developed with exclusive site-selectivity and excellent E-stereoselectivity. It was found that the olefination occurred at the acidic C-7 position only, overriding a potential directing-group assisted bias. With the wide range of alkene patterns, the protocol allows convenient access to multifarious C-7 olefinated benzo[d]isoxazoles in moderate to good yields.

Graphical abstract: Palladium-catalyzed site-selective direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[d]isoxazoles

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Publication details

The article was received on 02 Jun 2017, accepted on 26 Jun 2017 and first published on 27 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00435D
Citation: Org. Chem. Front., 2017, Advance Article
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    Palladium-catalyzed site-selective direct olefination of 6-electron-withdrawing group substituted 3-arylbenzo[d]isoxazoles

    Y. Guo, L. Shao, K. Yu, Y. Hu, H. Liu, D. Liao and Y. Ji, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00435D

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