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Issue 28, 2017
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Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

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Abstract

Utilizing rhodium catalysis, aryl nucleophiles generated via carbon–carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon–carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.

Graphical abstract: Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

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Publication details

The article was received on 17 May 2017, accepted on 24 Jun 2017 and first published on 26 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01212H
Citation: Org. Biomol. Chem., 2017,15, 5944-5948
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    Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

    C. E. Gregerson, K. N. Trentadue, E. J. T. Phipps, J. K. Kirsch, K. M. Reed, G. D. Dyke, J. H. Jansen, C. B. Otteman, J. L. Stachowski and J. B. Johnson, Org. Biomol. Chem., 2017, 15, 5944
    DOI: 10.1039/C7OB01212H

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