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Ru(II)-Catalyzed C H Activation: Amide-Directed 1,4-Addition of the Ortho C H Bond to Maleimides

Keshri, Puspam and Bettadapur, Kiran R and Lanke, Veeranjaneyulu and Prabhu, Kandikere Ramaiah (2016) Ru(II)-Catalyzed C H Activation: Amide-Directed 1,4-Addition of the Ortho C H Bond to Maleimides. In: JOURNAL OF ORGANIC CHEMISTRY, 81 (14). pp. 6056-6065.

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Official URL: http://dx.doi.org/10.1021/acs.joc.6b01160

Abstract

Maleimide has been used as a selective coupling partner to generate conjugate addition products exclusively. The typical Heck-type oxidative coupling that occurs when alkenes are used is avoided by choosing maleimide as an alkene, which cannot undergo beta-hydride elimination due to the unavailability of a syn-periplanar beta-hydrogen atom. The amide nitrogen, which is notorious for undergoing tandem reactions to generate spirocyclic or annulation products under cross-coupling conditions, remains innocent in this report. Along with the substrate scope, a robustness screen has been performed to analyze the performance of amide as a directing group in the presence of other directing groups and also to examine the tolerance of the reaction conditions for other frequently encountered functional groups.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 24 Aug 2016 10:22
Last Modified: 24 Aug 2016 10:22
URI: http://eprints.iisc.ac.in/id/eprint/54517

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