Copper‐Catalyzed Site‐Selective Intramolecular Amidation of Unactivated C(sp3)H Bonds1. (3rd March 2014)

• Record Type: Journal Article
• Authors: Wu, Xuesong; Zhao, Yan; Zhang, Guangwu; Ge, Haibo
• Is Part Of: Angewandte Chemie. Volume 126:Number 14(2014)
• Page Start: 3780
• Page End: 3784
• Publication Date: 2014-03-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201311263
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper‐catalyzed sp³ CH bond functionalization process. The reaction favors predominantly the CH bonds of β‐methyl groups over the unactivated methylene CH bonds. Moreover, a preference for activating sp³ CH bonds of β‐methyl groups, via a five‐membered ring intermediate, over the aromatic sp² CH bonds was also observed in the cyclometalation step. Additionally, sp³ CH bonds of unactivated secondary sp³ CH bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms.</p> </abstract>