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Title: Synthetic organic reactions mediated by sodium hydride
Authors: Ong, Derek Yiren
Pang, Jia Hao
Chiba, Shunsuke
Keywords: Science::Chemistry
Issue Date: 2019
Source: Ong, D. Y., Pang, J. H. & Chiba, S. (2019). Synthetic organic reactions mediated by sodium hydride. Journal of Synthetic Organic Chemistry, Japan 有機合成化学協会誌, 77(11), 1060-1069.
Project: 2015-T1-001-040
Journal: Journal of Synthetic Organic Chemistry, Japan 有機合成化学協会誌
Abstract: In synthetic organic chemistry, sodium hydride (NaH) has been utilized almost exclusively as a routine Brønsted base, while NaH has not been considered to work as a hydride donor. Recently, our group has serendipitously found that NaH can function as a unique hydride donor by its solvothermal treatment with sodium iodide (NaI) or lithium iodide (LiI) in tetrahydrofuran (THF) as a solvent. This discovery led to the development of unprecedented reductive molecular transformations such as hydrodecyanation of α-quaternary benzyl cyanides, controlled reduction of amides into aldehydes, dearylation of arylphopsphine oxides, and hydrodehalogenation of haloarenes. Moreover, this concise protocol allows for the use of NaH as enhanced Lewis acid and Brønsted base, enabling directed aromatic C-H sodiation, nucleophilic amination of methoxy arenes, and C2-amination of pyridines (the Chichibabin amination).
ISSN: 1883-6526
DOI: 10.5059/yukigoseikyokaishi.77.1060
Schools: School of Physical and Mathematical Sciences 
Rights: © 2019 The Society of Synthetic Organic Chemistry. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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