Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes
A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substit...
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sg-ntu-dr.10356-1548322023-02-28T19:58:18Z Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes Wang, Bin Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Allenes Enynes A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Nanyang Technological University (NTU) (for S.C.) and the Singapore Ministry of Education (Academic Research Fund Tier 2: MOE2019-T2-1-089 for S.C.) as well as JSPS KAKENHI grant JP19K06992 (for R.T.) and the Naito Foundation (for R.T.). 2022-01-17T06:44:40Z 2022-01-17T06:44:40Z 2021 Journal Article Wang, B., Li, Y., Pang, J. H., Watanabe, K., Takita, R. & Chiba, S. (2021). Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes. Angewandte Chemie International Edition, 60(1), 217-221. https://dx.doi.org/10.1002/anie.202012027 1433-7851 https://hdl.handle.net/10356/154832 10.1002/anie.202012027 32936502 2-s2.0-85096680098 1 60 217 221 en MOE2019-T2-1-089 Angewandte Chemie International Edition This is the peer reviewed version of the following article: Wang, B., Li, Y., Pang, J. H., Watanabe, K., Takita, R. & Chiba, S. (2021). Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes. Angewandte Chemie International Edition, 60(1), 217-221, which has been published in final form at https://doi.org/10.1002/anie.202012027. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf |
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Science::Chemistry Allenes Enynes Wang, Bin Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| description |
A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Wang, Bin Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke |
| format |
Article |
| author |
Wang, Bin Li, Yihang Pang, Jia Hao Watanabe, Kohei Takita, Ryo Chiba, Shunsuke |
| author_sort |
Wang, Bin |
| title |
Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| title_short |
Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| title_full |
Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| title_fullStr |
Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| title_full_unstemmed |
Hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| title_sort |
hydromagnesiation of 1,3-enynes by magnesium hydride for synthesis of tri- and tetra-substituted allenes |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/154832 |
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1759856277657223168 |