Issue 28, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
17 May 2017
Accepted
24 Jun 2017
First published
26 Jun 2017

Org. Biomol. Chem., 2017,15, 5944-5948

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements