Synthesis 2023; 55(09): 1451-1459
DOI: 10.1055/a-1988-5764
paper

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

Fan Luo
a   Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and State Key Laboratory of Bioengineering Reactor, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, P. R. China
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
,
Xiaobei Chen
a   Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and State Key Laboratory of Bioengineering Reactor, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, P. R. China
,
Jing Yu
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
,
Yuejia Yin
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
,
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
,
Ying Hu
c   Department of Pharmacy, Suzhou Vocational Health College, 28 Kehua Road, Suzhou 215009, P. R. China
,
Xuejun Liu
d   Shanghai Neutan Pharmaceutical Co., Ltd., Building 26, No. 555 Huanqiao Road, Pudong New Area, Shanghai 201315, P. R. China
,
Xiaodong Chen
d   Shanghai Neutan Pharmaceutical Co., Ltd., Building 26, No. 555 Huanqiao Road, Pudong New Area, Shanghai 201315, P. R. China
,
Shilei Zhang
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
,
Yanwei Hu
b   Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (22271206 and 22071053), Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission, grant 2021 Sci & Tech 03-28), East China University of Science and Technology, the ‘111’ Project and PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu­ Higher Education Institutions).


Abstract

An efficient and convenient palladium-catalyzed reductive system by employing sodium hydride as the hydrogen donor and acetic anhydride as an activator has been developed for transfer hydrogenation and acetylation of a wide range of N-heteroarenes including quinoline, phthalazine, quinoxaline, phenazine, phenanthridine, and indole. Moreover, acridine substrates could be directly reduced without the use of acetic anhydride. This protocol provides a simple method for the preparation of various saturated N-heterocycles.

Supporting Information



Publication History

Received: 06 September 2022

Accepted after revision: 28 November 2022

Accepted Manuscript online:
28 November 2022

Article published online:
03 January 2023

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