Copper-Catalyzed Site-Selective Intramolecular Amidation of Unactivated C(sp3)H Bonds†
Correction(s) for this article
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Berichtigung: Copper-Catalyzed Site-Selective Intramolecular Amidation of Unactivated C(sp3)H Bonds
- Volume 127Issue 9Angewandte Chemie
- pages: 2615-2615
- First Published online: February 17, 2015
Dr. Xuesong Wu
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorYan Zhao
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorDr. Guangwu Zhang
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Haibo Ge
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Institute of Chemistry and BioMedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China)
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)Search for more papers by this authorDr. Xuesong Wu
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorYan Zhao
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorDr. Guangwu Zhang
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. Haibo Ge
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
Institute of Chemistry and BioMedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China)
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)Search for more papers by this authorWe gratefully acknowledge Indiana University Purdue University Indianapolis for financial support. The Bruker 500 MHz NMR was purchased using funds from an NSF-MRI award (CHE-0619254).
Abstract
The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp3 CH bond functionalization process. The reaction favors predominantly the CH bonds of β-methyl groups over the unactivated methylene CH bonds. Moreover, a preference for activating sp3 CH bonds of β-methyl groups, via a five-membered ring intermediate, over the aromatic sp2 CH bonds was also observed in the cyclometalation step. Additionally, sp3 CH bonds of unactivated secondary sp3 CH bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms.
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