Developing the catalytic asymmetric hydroarsination reaction
The asymmetric hydroarsination reaction is arguably the most atom-economical and efficient manner to produce chiral arsines with high enantiopurities. Although various catalysts have been developed for the analogous hydrophosphination reaction, none have been effective for the hydroarsination reacti...
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Nanyang Technological University
2020
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sg-ntu-dr.10356-1428982023-02-28T23:32:18Z Developing the catalytic asymmetric hydroarsination reaction Tay, Wee Shan Leung Pak Hing Pullarkat Appukuttan Sumod School of Physical and Mathematical Sciences pakhing@ntu.edu.sg, Sumod@ntu.edu.sg Science::Chemistry::Organic chemistry::Organometallic compounds The asymmetric hydroarsination reaction is arguably the most atom-economical and efficient manner to produce chiral arsines with high enantiopurities. Although various catalysts have been developed for the analogous hydrophosphination reaction, none have been effective for the hydroarsination reaction thus far. Herein, the development of organometallic (Pd- and Ni- based) and organic (phosphine-based) catalytic systems for the hydroarsination reaction is discussed. Mechanistic investigations reveal that arsines were not direct substitutes of phosphines in this instance. Consequently, arsines were applied in several novel applications such as in deuteration, decomplexation and as a directing group. The relevance of these developments to general synthetic chemistry is also outlined. Doctor of Philosophy 2020-07-07T06:45:51Z 2020-07-07T06:45:51Z 2020 Thesis-Doctor of Philosophy Tay, W. S (2020). Developing the catalytic asymmetric hydroarsination reaction. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/142898 10.32657/10356/142898 en This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). application/pdf Nanyang Technological University |
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Science::Chemistry::Organic chemistry::Organometallic compounds |
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Science::Chemistry::Organic chemistry::Organometallic compounds Tay, Wee Shan Developing the catalytic asymmetric hydroarsination reaction |
| description |
The asymmetric hydroarsination reaction is arguably the most atom-economical and efficient manner to produce chiral arsines with high enantiopurities. Although various catalysts have been developed for the analogous hydrophosphination reaction, none have been effective for the hydroarsination reaction thus far. Herein, the development of organometallic (Pd- and Ni- based) and organic (phosphine-based) catalytic systems for the hydroarsination reaction is discussed. Mechanistic investigations reveal that arsines were not direct substitutes of phosphines in this instance. Consequently, arsines were applied in several novel applications such as in deuteration, decomplexation and as a directing group. The relevance of these developments to general synthetic chemistry is also outlined. |
| author2 |
Leung Pak Hing |
| author_facet |
Leung Pak Hing Tay, Wee Shan |
| format |
Thesis-Doctor of Philosophy |
| author |
Tay, Wee Shan |
| author_sort |
Tay, Wee Shan |
| title |
Developing the catalytic asymmetric hydroarsination reaction |
| title_short |
Developing the catalytic asymmetric hydroarsination reaction |
| title_full |
Developing the catalytic asymmetric hydroarsination reaction |
| title_fullStr |
Developing the catalytic asymmetric hydroarsination reaction |
| title_full_unstemmed |
Developing the catalytic asymmetric hydroarsination reaction |
| title_sort |
developing the catalytic asymmetric hydroarsination reaction |
| publisher |
Nanyang Technological University |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/142898 |
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1759853030386171904 |