Catalyst-Controlled, Regiodivergent Aminooxygenation Reactions of Dienes
Caitlyn P. McNichol, Liván Borrego, Erhan Ertekin, Shauna M. Paradine
TL;DR
This paper introduces a new chemical reaction method where changing the copper catalyst controls which product is formed from a single starting material.
Contribution
The novel contribution is using different copper catalysts to selectively produce either 1,2- or 1,4-aminooxygenated products from the same diene.
Findings
Switching the copper catalyst source leads to different regiochemical outcomes in aminooxygenation reactions.
The coordinating ligand on the copper salt determines the regioselectivity of the reaction.
Regiodivergence arises from competing mechanisms for oxygen delivery to a carbon-centered radical intermediate.
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.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Synthesis and Catalytic Reactions · Radical Photochemical Reactions