Pd-Catalyzed γ‑Acetoxylation of Alkylamides: Structural Influence of Directing Groups

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 h...

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Published inJournal of organic chemistry Vol. 87; no. 9; pp. 6378 - 6386
Main Authors Liu, Peng-Yu, Zhao, Shi-Chen, Zhang, Ming-Yuan, Song, Lijuan, Wang, Caiping, Yu, Fang, Meng, Qingtao, Zhang, Zhiqiang, He, Yu-Peng
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.05.2022
Subjects
group effect
organic chemistry
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.2c00085

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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.
AbstractList 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.
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.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.
Author Song, Lijuan
Meng, Qingtao
Liu, Peng-Yu
Wang, Caiping
Zhang, Zhiqiang
He, Yu-Peng
Zhang, Ming-Yuan
Zhao, Shi-Chen
Yu, Fang
AuthorAffiliation Key Laboratory of Petrochemical Catalytic Science and Technology
Key Laboratory for Functional Material, Educational Department of Liaoning Province, School of Chemical Engineering
State Key Laboratory Fine Chemicals
Beijing Winsunny Pharmaceutical CO., LTD
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SubjectTerms group effect
organic chemistry
Title Pd-Catalyzed γ‑Acetoxylation of Alkylamides: Structural Influence of Directing Groups
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