Nickel-Catalyzed Site-Selective Amidation of Unactivated C(sp3)H Bonds

Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel‐catalyzed CH bond functionalization process with the assistance of a bidentate directing group. The reaction favors the CH bonds of β‐methyl groups over the γ‐methyl or β‐methyle...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-07, Vol.20 (31), p.9530-9533
Main Authors: Wu, Xuesong, Zhao, Yan, Ge, Haibo
Format: Article
Language:English
Subjects:
Aliphatic compounds
amidation
Amides
Beta
Carbon
Catalysis
Chemical bonds
Chemistry
CH bond functionalization
Dehydrogenation
Nickel
site selectivity
β-lactams
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Summary:Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel‐catalyzed CH bond functionalization process with the assistance of a bidentate directing group. The reaction favors the CH bonds of β‐methyl groups over the γ‐methyl or β‐methylene groups. Additionally, a predominant preference for the β‐methyl CH bonds over the aromatic sp2 CH bonds was observed. Moreover, this process also allows for the effective functionalization of benzylic secondary sp3 CH bonds. β‐Lactams from nickel catalysis: Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel‐catalyzed CH bond functionalization process with the assistance of a bidentate directing group (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403356