Pd-Catalyzed γ-Acetoxylation of Alkylamides: Structural Influence of Directing Groups.
J Org Chem
; 87(9): 6378-6386, 2022 May 06.
Article
em En
| MEDLINE
| ID: mdl-35422116
ABSTRACT
Although direct acetoxylation and cyclization of alkylamide have been extensively reported, investigation of the structural influence of directing groups on selectivity is limited. Pd-catalyzed 2-methoxyiminoacyl (MIA) assisted γ-acetoxylation of alkylamides has been developed. Further DFT studies have demonstrated that the directing groups have a significant influence on the reductive elimination step. The strong electron-donating effect of the OMe group in MIA leads to the preferential formation of a five-membered cyclopalladium (OAc-Pd-C) complex, which favors the acetoxylation pathway.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2022
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Article