Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 14, Pages 3706-3710Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201311263
Keywords
CH activation; copper; heterocycles; homogeneous catalysis; synthetic methods
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Funding
- Indiana University Purdue University Indianapolis
- NSF-MRI award [CHE-0619254]
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The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp(3) CH bond functionalization process. The reaction favors predominantly the CH bonds of -methyl groups over the unactivated methylene CH bonds. Moreover, a preference for activating sp(3) CH bonds of -methyl groups, via a five-membered ring intermediate, over the aromatic sp(2) CH bonds was also observed in the cyclometalation step. Additionally, sp(3) CH bonds of unactivated secondary sp(3) CH bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms.
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