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

Tobias Pinkert; Tristan Wegner; Shobhan Mondal; Frank Glorius

doi:10.1002/anie.201907269

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

Angew Chem Int Ed Engl. 2019 Oct 14;58(42):15041-15045. doi: 10.1002/anie.201907269. Epub 2019 Sep 5.

Authors

Tobias Pinkert¹, Tristan Wegner¹, Shobhan Mondal¹, Frank Glorius¹

Affiliation

¹ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.

PMID: 31389654
DOI: 10.1002/anie.201907269

Abstract

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.

Keywords: C−H activation; carboamination; diastereoselectivity; dienes; multicomponent reactions.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding