Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation
Carbyne, an interesting synthetic intermediate, has recently been generated from hypervalent iodine precursors via photoredox catalysis. Given the underexplored chemistry of carbyne, due to the paucity of carbyne sources, we are intrigued to discover a new source for this reactive species from class...
| Main Authors: | , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2019
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/105516 http://hdl.handle.net/10220/47810 |
| _version_ | 1826115535871410176 |
|---|---|
| author | Das, Mrinmoy Vu, Minh Duy Zhang, Qi Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Das, Mrinmoy Vu, Minh Duy Zhang, Qi Liu, Xue-Wei |
| author_sort | Das, Mrinmoy |
| collection | NTU |
| description | Carbyne, an interesting synthetic intermediate, has recently been generated from hypervalent iodine precursors via photoredox catalysis. Given the underexplored chemistry of carbyne, due to the paucity of carbyne sources, we are intrigued to discover a new source for this reactive species from classical reagents – phosphonium ylides. Our novel strategy employing phosphonium ylides in an olefin hydrocarbonation reaction features a facile approach for constructing carbon–carbon bonds through metal-free and benign reaction conditions. Moreover, the hydrocarbonation products were delivered in a highly regioselective manner. |
| first_indexed | 2024-10-01T03:56:45Z |
| format | Journal Article |
| id | ntu-10356/105516 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:56:45Z |
| publishDate | 2019 |
| record_format | dspace |
| spelling | ntu-10356/1055162023-02-28T19:43:28Z Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation Das, Mrinmoy Vu, Minh Duy Zhang, Qi Liu, Xue-Wei School of Physical and Mathematical Sciences Phosphonium Ylide Photoredox DRNTU::Science::Chemistry Carbyne, an interesting synthetic intermediate, has recently been generated from hypervalent iodine precursors via photoredox catalysis. Given the underexplored chemistry of carbyne, due to the paucity of carbyne sources, we are intrigued to discover a new source for this reactive species from classical reagents – phosphonium ylides. Our novel strategy employing phosphonium ylides in an olefin hydrocarbonation reaction features a facile approach for constructing carbon–carbon bonds through metal-free and benign reaction conditions. Moreover, the hydrocarbonation products were delivered in a highly regioselective manner. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) Published version 2019-03-14T06:15:44Z 2019-12-06T21:52:50Z 2019-03-14T06:15:44Z 2019-12-06T21:52:50Z 2019 Journal Article Das, M., Vu, M. D., Zhang, Q., & Liu, X.-W. (2019). Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation . Chemical Science, 10(6), 1687-1691. doi:10.1039/C8SC04195D 2041-6520 https://hdl.handle.net/10356/105516 http://hdl.handle.net/10220/47810 10.1039/C8SC04195D en Chemical Science © 2019 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. 5 p. application/pdf |
| spellingShingle | Phosphonium Ylide Photoredox DRNTU::Science::Chemistry Das, Mrinmoy Vu, Minh Duy Zhang, Qi Liu, Xue-Wei Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation |
| title | Metal-free visible light photoredox enables generation of carbyne equivalents
via
phosphonium ylide C–H activation |
| title_full | Metal-free visible light photoredox enables generation of carbyne equivalents
via
phosphonium ylide C–H activation |
| title_fullStr | Metal-free visible light photoredox enables generation of carbyne equivalents
via
phosphonium ylide C–H activation |
| title_full_unstemmed | Metal-free visible light photoredox enables generation of carbyne equivalents
via
phosphonium ylide C–H activation |
| title_short | Metal-free visible light photoredox enables generation of carbyne equivalents
via
phosphonium ylide C–H activation |
| title_sort | metal free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide c h activation |
| topic | Phosphonium Ylide Photoredox DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/105516 http://hdl.handle.net/10220/47810 |
| work_keys_str_mv | AT dasmrinmoy metalfreevisiblelightphotoredoxenablesgenerationofcarbyneequivalentsviaphosphoniumylidechactivation AT vuminhduy metalfreevisiblelightphotoredoxenablesgenerationofcarbyneequivalentsviaphosphoniumylidechactivation AT zhangqi metalfreevisiblelightphotoredoxenablesgenerationofcarbyneequivalentsviaphosphoniumylidechactivation AT liuxuewei metalfreevisiblelightphotoredoxenablesgenerationofcarbyneequivalentsviaphosphoniumylidechactivation |