Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides
A concise protocol for anti-hydromagnesiation of aryl alkynes was established using 1 : 1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophi...
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sg-ntu-dr.10356-1548342023-02-28T19:58:29Z Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides Wang, Bin Ong, Derek Yiren Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Catalysts Hydrides A concise protocol for anti-hydromagnesiation of aryl alkynes was established using 1 : 1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process. Ministry of Education (MOE) Nanyang Technological University Published version This work was supported by funding from Nanyang Techno- logical University (NTU) and the Singapore Ministry of Educa- tion (Academic Research Fund Tier 2: MOE2019-T2-1-089) (for S. C.) as well as JSPS (Grant-in-Aid for Scientic Research (C) (19K0662)), Uehara Memorial Foundation, and the Naito Foundation (for R. T.). The computations were performed using Research Center for Computational Science at Okazaki, Japan. 2022-01-13T06:46:22Z 2022-01-13T06:46:22Z 2020 Journal Article Wang, B., Ong, D. Y., Li, Y., Pang, J. H., Watanabe, K., Takita, R. & Chiba, S. (2020). Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides. Chemical Science, 11(20), 5267-5272. https://dx.doi.org/10.1039/d0sc01773f 2041-6520 https://hdl.handle.net/10356/154834 10.1039/d0sc01773f 34122983 2-s2.0-85085646938 20 11 5267 5272 en MOE2019-T2-1-089 Chemical Science © 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License. application/pdf |
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Science::Chemistry Catalysts Hydrides Wang, Bin Ong, Derek Yiren Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| description |
A concise protocol for anti-hydromagnesiation of aryl alkynes was established using 1 : 1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Wang, Bin Ong, Derek Yiren Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke |
| format |
Article |
| author |
Wang, Bin Ong, Derek Yiren Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke |
| author_sort |
Wang, Bin |
| title |
Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| title_short |
Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| title_full |
Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| title_fullStr |
Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| title_full_unstemmed |
Stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| title_sort |
stereo-controlled anti-hydromagnesiation of aryl alkynes by magnesium hydrides |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/154834 |
| _version_ |
1759855180092801024 |