Palladium‐Catalyzed β‐C−H Arylation of Ketones Using Amino Amide as a Transient Directing Group: Applications to Synthesis of Phenanthridinone Alkaloids

The direct arylation of aromatic and aliphatic ketones was carried out via palladium‐catalyzed inert C−H bond functionalization with 2‐amino‐N‐isopropyl‐acetamide as a new catalytic transient directing group. The reaction showed excellent functional group compatibility and site selectivity. We demon...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-10, Vol.360 (19), p.3709-3715
Main Authors: Wang, Junliang, Dong, Cong, Wu, Liangfei, Xu, Mingkai, Lin, Jun, Wei, Kun
Format: Article
Language:English
Subjects:
Aliphatic compounds
Alkaloids
arylation of ketones
Catalysis
Catalysts
Chemical synthesis
Functional groups
Hydrogen bonds
Ketones
Organic chemistry
Palladium
palladium-catalyzed
phenanthridinone alkaloids
transient directing group
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Summary:The direct arylation of aromatic and aliphatic ketones was carried out via palladium‐catalyzed inert C−H bond functionalization with 2‐amino‐N‐isopropyl‐acetamide as a new catalytic transient directing group. The reaction showed excellent functional group compatibility and site selectivity. We demonstrated that α‐amino amide forming N,N‐bidentate coordination with Pd catalyst is more favorable for the β‐arylation of ketones than α‐amino acid forming N,O‐bidentate coordination with Pd catalyst under relatively mild conditions. This elegant approach provides straightforward access to important structural motifs in organic and medicinal chemistry and is demonstrated here in the efficient synthesis of phenanthridinone alkaloids.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800489