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

Angewandte Chemie
Tobias PinkertFrank Glorius

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 RhIII -allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion.

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Citations

Feb 15, 2020·Chemistry, an Asian Journal·Sunliang CuiYuxin Lin
Mar 21, 2020·Chemistry : a European Journal·Hui XieJun Wang
Nov 6, 2020·Chemical Communications : Chem Comm·Prasun Mukherjee, Debabrata Maiti
Dec 8, 2020·Chemical Communications : Chem Comm·Yixin CuiXingwei Li
Jan 6, 2021·Angewandte Chemie·Shobhan MondalFrank Glorius
May 12, 2021·Journal of the American Chemical Society·Tobias PinkertFrank Glorius
Aug 21, 2021·Journal of the American Chemical Society·Taeho KangKeary M Engle
Jan 10, 2020·The Journal of Organic Chemistry·Sonbidya BanerjeeTharmalingam Punniyamurthy

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