Related Experiment Video
Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalyst-Controlled, Regiodivergent Aminooxygenation Reactions of Dienes
Caitlyn P McNichol1, Liván Borrego1, Erhan Ertekin1
1Department of Chemistry, University of Rochester, 120 Trustee Rd, Rochester, New York 14627, United States.
Abstract:
We report a method for an aerobic, regiodivergent aminooxygenation of dienes via catalyst control. A simple switch in the copper catalyst source allows for selective access to either the 1,2- or 1,4-aminooxygenated product from a single starting material. Mechanistic studies indicate that the coordinating ligand on the copper salt is responsible for the divergent regiochemical outcomes and that the origin of regiodivergence lies in competing mechanisms for oxygen delivery to the carbon-centered radical intermediate.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

