Urea‐Induced Acid Amplification: A New Approach for Metal‐Free Insertion Chemistry. Issue 27 (30th May 2014)

• Record Type: Journal Article
• Authors: Couch, Erica D.; Auvil, Tyler J.; Mattson, Anita E.
• Is Part Of: Chemistry. Volume 20:Issue 27(2014)
• Page Start: 8283
• Page End: 8287
• Publication Date: 2014-05-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201403283
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The enhanced catalytic activity of difluoroboronate ureas proved to be essential as an acidity amplifier to promote metal‐free OH and SH insertion reactions of α‐aryldiazoacetates in high yield. This methodology was found to be generally applicable to a broad substrate scope and presents a conceptually new approach for organocatalytic diazo insertion reactions. Mechanistic investigations suggest that the reaction pathway involves a urea‐induced protonation of the α‐aryldiazoester.</p> </abstract>