A Biomimetic Catalytic Aerobic Functionalization of Phenols1. Issue 23 (17th April 2014)

• Record Type: Journal Article
• Authors: Esguerra, Kenneth Virgel N.; Fall, Yacoub; Lumb, Jean‐Philip
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 23(2014)
• Page Start: 5877
• Page End: 5881
• Publication Date: 2014-04-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201311103
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The importance of aromatic CO, CN, and CS bonds necessitates increasingly efficient strategies for their formation. Herein, we report a biomimetic approach that converts phenolic CH bonds into CO, CN, and CS bonds at the sole expense of reducing dioxygen (O₂) to water (H₂O). Our method hinges on a regio‐ and chemoselective copper‐catalyzed aerobic oxygenation to provide <italic>ortho</italic>‐quinones. <italic>ortho</italic>‐Quinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings.</p> </abstract>