Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes
A transition metal-free dehydrative allylation of stabilized P-ylides with activated allylic alcohols has been developed. This protocol utilizes a calcium catalyst to facilitate the cleavage of C-OH bonds and enables smooth dehydrative cross-coupling with P-ylides, resulting in water as the sole by-...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/173495 |
| _version_ | 1826122354890113024 |
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| author | Li, Xiaohong Zhang, Dong Wang, Yan Xiao, Shiji Wu, Ying Xie, Peizhong Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Li, Xiaohong Zhang, Dong Wang, Yan Xiao, Shiji Wu, Ying Xie, Peizhong Loh, Teck-Peng |
| author_sort | Li, Xiaohong |
| collection | NTU |
| description | A transition metal-free dehydrative allylation of stabilized P-ylides with activated allylic alcohols has been developed. This protocol utilizes a calcium catalyst to facilitate the cleavage of C-OH bonds and enables smooth dehydrative cross-coupling with P-ylides, resulting in water as the sole by-product. Remarkably, this transformation exhibits excellent tolerance towards a diverse range of allylic alcohols and P-ylides. Furthermore, the subsequent Wittig reaction affords a wide array of highly functionalized 1,4-dienes with high yields. |
| first_indexed | 2024-10-01T05:46:48Z |
| format | Journal Article |
| id | ntu-10356/173495 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:46:48Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1734952024-02-07T04:47:58Z Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes Li, Xiaohong Zhang, Dong Wang, Yan Xiao, Shiji Wu, Ying Xie, Peizhong Loh, Teck-Peng School of Physical and Mathematical Sciences Chemistry Allylic Alcohol Wittig Reaction A transition metal-free dehydrative allylation of stabilized P-ylides with activated allylic alcohols has been developed. This protocol utilizes a calcium catalyst to facilitate the cleavage of C-OH bonds and enables smooth dehydrative cross-coupling with P-ylides, resulting in water as the sole by-product. Remarkably, this transformation exhibits excellent tolerance towards a diverse range of allylic alcohols and P-ylides. Furthermore, the subsequent Wittig reaction affords a wide array of highly functionalized 1,4-dienes with high yields. We gratefully acknowledge financial support from the National Natural Science Foundation of China (21702108), Natural Science Foundation of Jiangsu Province, China (BK20211257), and the Six Talent Peaks Project in Jiangsu Province (YY-033). 2024-02-07T04:47:57Z 2024-02-07T04:47:57Z 2023 Journal Article Li, X., Zhang, D., Wang, Y., Xiao, S., Wu, Y., Xie, P. & Loh, T. (2023). Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes. New Journal of Chemistry, 47(40), 18779-18784. https://dx.doi.org/10.1039/d3nj03640e 1144-0546 https://hdl.handle.net/10356/173495 10.1039/d3nj03640e 2-s2.0-85174409817 40 47 18779 18784 en New Journal of Chemistry © 2023 The Author(s). All rights reserved. |
| spellingShingle | Chemistry Allylic Alcohol Wittig Reaction Li, Xiaohong Zhang, Dong Wang, Yan Xiao, Shiji Wu, Ying Xie, Peizhong Loh, Teck-Peng Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title | Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title_full | Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title_fullStr | Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title_full_unstemmed | Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title_short | Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes |
| title_sort | calcium catalyzed dehydrative allylation of p ylides and sequential wittig reaction for streamlined access to versatile 1 4 dienes |
| topic | Chemistry Allylic Alcohol Wittig Reaction |
| url | https://hdl.handle.net/10356/173495 |
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