Aromatic substituent effects in palladium-catalyzed intramolecular olefin oxyarylation reactions. Issue 13 (26th March 2020)

• Record Type: Journal Article
• Authors: Maust, Mark C.; Croft, Zacary L.; Sullivan, Mackenzie W.; Dove, Ross L.; Hardy, Emily E.; Brenzovich, W.E.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 13(2020)
• Publication Date: 2020-03-26
• Subjects: Palladium -- Olefin difunctionalization -- Oxidative -- Cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151674
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Palladium-catalyzed oxyarylation can be accomplished in an intramolecular fashion. High oxidation-state palladium catalysis can initiate an aryl rearrangements. The regiochemistry of aryl addition is highly dependent on electron-donating groups. Abstract: The effect of electron-donating groups on the palladium-catalyzed intramolecular oxyarylation reaction was studied. In the case of activation at the ortho -position, the reaction favors the formation of a tricyclic lactone via CH insertion. However, when the ipso -position is activated, the major product is instead a novel α, β-unsaturated lactone formed by way of a stabilized phenonium intermediate followed by elimination.