4.8 Article

Intermolecular 1,4-Carboamination of Conjugated Dienes Enabled by Cp*RhIII-Catalyzed C-H Activation

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 42, Pages 15041-15045

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907269

Keywords

carboamination; C-H activation; diastereoselectivity; dienes; multicomponent reactions

Funding

  1. Deutsche Forschungsgemeinschaft (Leibniz Award) [SFB 858]
  2. WWU Munster (Graduate School of Molecules and Interfaces)

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A protocol for the three-component 1,4-carboamination of dienes is described. Synthetically versatile Weinreb amides were coupled with 1,3-dienes and readily available dioxazolones as the nitrogen source using [Cp*RhCl2](2)-catalyzed C-H activation to deliver the 1,4-carboaminated products. This transformation proceeds under mild reaction conditions and affords the products with high levels of regio- and E-selectivity. Mechanistic investigations suggest an intermediate Rh-III-allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion.

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