Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes
A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/139270 |
| _version_ | 1824454088299905024 |
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| author | Wang, Chengdong Xiao, Guanlin Guo, Tao Ding, Yalan Wu, Xiaojin Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Wang, Chengdong Xiao, Guanlin Guo, Tao Ding, Yalan Wu, Xiaojin Loh, Teck-Peng |
| author_sort | Wang, Chengdong |
| collection | NTU |
| description | A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling process is stereoretentive for the alkyl chain. Mechanistically, alkyl palladacycle intermediates stabilized by directing group and ligand, hydride species multigenerated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity. |
| first_indexed | 2025-02-19T03:16:45Z |
| format | Journal Article |
| id | ntu-10356/139270 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:16:45Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1392702020-05-18T07:48:03Z Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes Wang, Chengdong Xiao, Guanlin Guo, Tao Ding, Yalan Wu, Xiaojin Loh, Teck-Peng School of Physical and Mathematical Sciences Engineering::Chemical engineering Hydrocarbons Anions A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling process is stereoretentive for the alkyl chain. Mechanistically, alkyl palladacycle intermediates stabilized by directing group and ligand, hydride species multigenerated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity. MOE (Min. of Education, S’pore) 2020-05-18T07:48:03Z 2020-05-18T07:48:03Z 2018 Journal Article Wang, C., Xiao, G., Guo, T., Ding, Y., Wu, X., & Loh, T.-P. (2018). Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes. Journal of the American Chemical Society, 140(30), 9332-9336. doi:10.1021/jacs.8b03619 0002-7863 https://hdl.handle.net/10356/139270 10.1021/jacs.8b03619 29925236 2-s2.0-85048991149 30 140 9332 9336 en Journal of the American Chemical Society © 2018 American Chemical Society. All rights reserved. |
| spellingShingle | Engineering::Chemical engineering Hydrocarbons Anions Wang, Chengdong Xiao, Guanlin Guo, Tao Ding, Yalan Wu, Xiaojin Loh, Teck-Peng Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title | Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title_full | Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title_fullStr | Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title_full_unstemmed | Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title_short | Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes |
| title_sort | palladium catalyzed regiocontrollable reductive heck reaction of unactivated aliphatic alkenes |
| topic | Engineering::Chemical engineering Hydrocarbons Anions |
| url | https://hdl.handle.net/10356/139270 |
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