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

Fan Luo; Xiaobei Chen; Jing Yu; Yuejia Yin; Xiaoxiao Hu; Ying Hu; Xuejun Liu; Xiaodong Chen; Shilei Zhang; Yanwei Hu

doi:10.1055/a-1988-5764

Synthesis, Inhaltsverzeichnis

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‡

^aShanghai 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

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

,

Xiaobei Chen‡

^aShanghai 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

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

,

Yuejia Yin

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

,

Xiaoxiao Hu

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

,

Ying Hu∗

^cDepartment of Pharmacy, Suzhou Vocational Health College, 28 Kehua Road, Suzhou 215009, P. R. China

,

Xuejun Liu

^dShanghai Neutan Pharmaceutical Co., Ltd., Building 26, No. 555 Huanqiao Road, Pudong New Area, Shanghai 201315, P. R. China

,

Xiaodong Chen

^dShanghai Neutan Pharmaceutical Co., Ltd., Building 26, No. 555 Huanqiao Road, Pudong New Area, Shanghai 201315, P. R. China

,

Shilei Zhang∗

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

,

Yanwei Hu∗

^bJiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, P. R. China

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Abstract

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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.

Key word

palladium - sodium hydride - transfer hydrogenation - N-heteroarenes - N-heterocycles

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