Synthetic organic reactions mediated by sodium hydride
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 treatm...
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| Format: | Journal Article |
| Language: | English |
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2022
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| Online Access: | https://hdl.handle.net/10356/154872 https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/11/77_1060/_pdf/-char/en |
| _version_ | 1811692146401476608 |
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| author | Ong, Derek Yiren Pang, Jia Hao Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Ong, Derek Yiren Pang, Jia Hao Chiba, Shunsuke |
| author_sort | Ong, Derek Yiren |
| collection | NTU |
| description | 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). |
| first_indexed | 2024-10-01T06:31:09Z |
| format | Journal Article |
| id | ntu-10356/154872 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:31:09Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1548722022-02-15T01:36:15Z Synthetic organic reactions mediated by sodium hydride Ong, Derek Yiren Pang, Jia Hao Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Sodium Hydride Synthetic Organic Chemistry 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). Ministry of Education (MOE) Nanyang Technological University This work was supported by funding from Nanyang Technological University (NTU) Singapore and the Singapore Ministry of Education (Academic Research Fund Tier 1: 2015─T1─001─040). We thank Prof. Ryo Takita (University of Tokyo) and Prof. Hajime Hirao (City University of Hong Kong) for their computational studies on our reactions. Our co─workers whose names appear in the references are gratefully acknowledged for their intellectual and experimental contributions. 2022-02-15T01:32:50Z 2022-02-15T01:32:50Z 2019 Journal Article 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. https://dx.doi.org/10.5059/yukigoseikyokaishi.77.1060 1883-6526 https://hdl.handle.net/10356/154872 10.5059/yukigoseikyokaishi.77.1060 2-s2.0-85083564975 https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/11/77_1060/_pdf/-char/en 11 77 1060 1069 en 2015-T1-001-040 Journal of Synthetic Organic Chemistry, Japan 有機合成化学協会誌 © 2019 The Society of Synthetic Organic Chemistry. All rights reserved. |
| spellingShingle | Science::Chemistry Sodium Hydride Synthetic Organic Chemistry Ong, Derek Yiren Pang, Jia Hao Chiba, Shunsuke Synthetic organic reactions mediated by sodium hydride |
| title | Synthetic organic reactions mediated by sodium hydride |
| title_full | Synthetic organic reactions mediated by sodium hydride |
| title_fullStr | Synthetic organic reactions mediated by sodium hydride |
| title_full_unstemmed | Synthetic organic reactions mediated by sodium hydride |
| title_short | Synthetic organic reactions mediated by sodium hydride |
| title_sort | synthetic organic reactions mediated by sodium hydride |
| topic | Science::Chemistry Sodium Hydride Synthetic Organic Chemistry |
| url | https://hdl.handle.net/10356/154872 https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/11/77_1060/_pdf/-char/en |
| work_keys_str_mv | AT ongderekyiren syntheticorganicreactionsmediatedbysodiumhydride AT pangjiahao syntheticorganicreactionsmediatedbysodiumhydride AT chibashunsuke syntheticorganicreactionsmediatedbysodiumhydride |