Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols
Being a handle for synthesizing quaternary carbon centers and olefins, together with ubiquitous appearance in organic building blocks, makes tertiary alcohols valuable targets in synthesis. However, traditional syntheses of these alcohols have faced several challenges including the employment of fun...
| Main Authors: | , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Online Access: | https://hdl.handle.net/10356/138401 |
| _version_ | 1811678990861074432 |
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| author | Vu, Minh Duy Das, Mrinmoy Guo, Aoxin Ang, Zi-En D̵okić, Miloš Soo, Han Sen Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Vu, Minh Duy Das, Mrinmoy Guo, Aoxin Ang, Zi-En D̵okić, Miloš Soo, Han Sen Liu, Xue-Wei |
| author_sort | Vu, Minh Duy |
| collection | NTU |
| description | Being a handle for synthesizing quaternary carbon centers and olefins, together with ubiquitous appearance in organic building blocks, makes tertiary alcohols valuable targets in synthesis. However, traditional syntheses of these alcohols have faced several challenges including the employment of functionalized reactive reagents, undesirable side reactions, and decomposition of the alcohol products under harsh conditions. The paucity of a synthetic approach to bulky tertiary alcohols prompts our interest to develop a benign catalytic protocol to tackle the current issues. Here, we have successfully demonstrated the use of ketyl radicals in intermolecular cross radical-radical coupling, which has opened a different door for accessing complex tertiary alcohols. On the other hand, by starting from feedstock and naturally derived chemicals without any pre-activation, it would be superior to traditional methodologies in the industrial context. |
| first_indexed | 2024-10-01T03:02:03Z |
| format | Journal Article |
| id | ntu-10356/138401 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:02:03Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1384012023-02-28T19:48:51Z Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols Vu, Minh Duy Das, Mrinmoy Guo, Aoxin Ang, Zi-En D̵okić, Miloš Soo, Han Sen Liu, Xue-Wei School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Photoredox Catalysis HAT Catalyst Being a handle for synthesizing quaternary carbon centers and olefins, together with ubiquitous appearance in organic building blocks, makes tertiary alcohols valuable targets in synthesis. However, traditional syntheses of these alcohols have faced several challenges including the employment of functionalized reactive reagents, undesirable side reactions, and decomposition of the alcohol products under harsh conditions. The paucity of a synthetic approach to bulky tertiary alcohols prompts our interest to develop a benign catalytic protocol to tackle the current issues. Here, we have successfully demonstrated the use of ketyl radicals in intermolecular cross radical-radical coupling, which has opened a different door for accessing complex tertiary alcohols. On the other hand, by starting from feedstock and naturally derived chemicals without any pre-activation, it would be superior to traditional methodologies in the industrial context. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-05-05T13:32:21Z 2020-05-05T13:32:21Z 2019 Journal Article Vu, M. D., Das, M., Guo, A., Ang, Z.-E., D̵okić, M., Soo, H. S., & Liu, X.-W. (2019). Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols. ACS Catalysis, 9(10), 9009-9014. doi:10.1021/acscatal.9b02401 2155-5435 https://hdl.handle.net/10356/138401 10.1021/acscatal.9b02401 2-s2.0-85072709232 10 9 9009 9014 en ACS Catalysis This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b02401 application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Photoredox Catalysis HAT Catalyst Vu, Minh Duy Das, Mrinmoy Guo, Aoxin Ang, Zi-En D̵okić, Miloš Soo, Han Sen Liu, Xue-Wei Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title | Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title_full | Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title_fullStr | Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title_full_unstemmed | Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title_short | Visible-light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| title_sort | visible light photoredox enables ketone carbonyl alkylation for easy access to tertiary alcohols |
| topic | Science::Chemistry::Organic chemistry Photoredox Catalysis HAT Catalyst |
| url | https://hdl.handle.net/10356/138401 |
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