Pd-Catalyzed Î³-Acetoxylation of Alkylamides: Structural Influence of Directing Groups.

Liu, Peng-Yu; Zhao, Shi-Chen; Zhang, Ming-Yuan; Song, Lijuan; Wang, Caiping; Yu, Fang; Meng, Qingtao; Zhang, Zhiqiang; He, Yu-Peng

Liu, Peng-Yu; Zhao, Shi-Chen; Zhang, Ming-Yuan; Song, Lijuan; Wang, Caiping; Yu, Fang; Meng, Qingtao; Zhang, Zhiqiang; He, Yu-Peng.

Afiliação

Liu PY; Key Laboratory for Functional Material, Educational Department of Liaoning Province, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China.
Zhao SC; Key Laboratory of Petrochemical Catalytic Science and Technology, Liaoning Petrochemical University, Dandong Load West 1, Fushun 113001, China.
Zhang MY; Key Laboratory of Petrochemical Catalytic Science and Technology, Liaoning Petrochemical University, Dandong Load West 1, Fushun 113001, China.
Song L; Key Laboratory of Petrochemical Catalytic Science and Technology, Liaoning Petrochemical University, Dandong Load West 1, Fushun 113001, China.
Wang C; Key Laboratory for Functional Material, Educational Department of Liaoning Province, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China.
Yu F; Key Laboratory of Petrochemical Catalytic Science and Technology, Liaoning Petrochemical University, Dandong Load West 1, Fushun 113001, China.
Meng Q; Beijing Winsunny Pharmaceutical CO., LTD, Beijing 101113, China.
Zhang Z; State Key Laboratory Fine Chemicals, Ningbo Institute of Dalian University of Technology, No. 26 Yucai Road, Jiangbei District, Ningbo 315016, China.
He YP; Key Laboratory for Functional Material, Educational Department of Liaoning Province, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China.

J Org Chem ; 87(9): 6378-6386, 2022 May 06.

Article em En | MEDLINE | ID: mdl-35422116

ABSTRACT

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 Î³-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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Texto completo: 1 Bases de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2022 Tipo de documento: Article País de afiliação: China