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

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 β-hydride elimination due to the unavailability...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-07, Vol.81 (14), p.6056-6065
Main Authors: Keshri, Puspam, Bettadapur, Kiran R, Lanke, Veeranjaneyulu, Prabhu, Kandikere Ramaiah
Format: Article
Language:English
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Summary: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 β-hydride elimination due to the unavailability of a syn-periplanar β-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01160