AI Article Synopsis
- Investigations into how different directing groups impact selectivity in the acetoxylation and cyclization of alkylamides are limited, despite extensive research on the reactions themselves.
- A new method using palladium (Pd) catalysis with 2-methoxyiminoacyl (MIA) has been developed for γ-acetoxylation of alkylamides.
- Density Functional Theory (DFT) studies reveal that the strength of the electron-donating OMe group in MIA significantly affects the reductive elimination step, encouraging the formation of a five-membered cyclopalladium complex that enhances the acetoxylation process.
Article 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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| http://dx.doi.org/10.1021/acs.joc.2c00085 | DOI Listing |
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