Pd-Catalyzed γ‑Acetoxylation of Alkylamides: Structural Influence of Directing Groups
The Journal of Organic Chemistry(2022)
摘要
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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