Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols
A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under m...
| Main Authors: | , , , , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Online Access: | https://hdl.handle.net/10356/155331 |
| _version_ | 1826115080584953856 |
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| author | Xie, Peizhong Sun, Zuolian Li, Shuangshuang Cai, Xinying Qiu, Ju Fu, Weishan Gao, Cuiqing Wu, Shisheng Yang, Xiaobo Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Xie, Peizhong Sun, Zuolian Li, Shuangshuang Cai, Xinying Qiu, Ju Fu, Weishan Gao, Cuiqing Wu, Shisheng Yang, Xiaobo Loh, Teck-Peng |
| author_sort | Xie, Peizhong |
| collection | NTU |
| description | A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration. |
| first_indexed | 2024-10-01T03:49:41Z |
| format | Journal Article |
| id | ntu-10356/155331 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:49:41Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1553312022-03-18T06:07:27Z Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols Xie, Peizhong Sun, Zuolian Li, Shuangshuang Cai, Xinying Qiu, Ju Fu, Weishan Gao, Cuiqing Wu, Shisheng Yang, Xiaobo Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Reciprocal-Activation Strategy Allylic Sulfination A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration. Ministry of Education (MOE) The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (21702108), the Natural Science Foundation of Jiangsu Province, China (BK20160977), the Six Talent Peaks Project gsu Province (YY-033), Grant MOE2016-T1-002-043 (RG111/16) from the Ministry of Education of Singapore, and Nanjing Tech University (39837101). 2022-03-18T06:07:27Z 2022-03-18T06:07:27Z 2020 Journal Article Xie, P., Sun, Z., Li, S., Cai, X., Qiu, J., Fu, W., Gao, C., Wu, S., Yang, X. & Loh, T. (2020). Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols. Organic Letters, 22(12), 4893-4897. https://dx.doi.org/10.1021/acs.orglett.0c01747 1523-7060 https://hdl.handle.net/10356/155331 10.1021/acs.orglett.0c01747 32496788 2-s2.0-85086584379 12 22 4893 4897 en 2016-T1-002-043 RG111/16 Organic Letters © 2020 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry Reciprocal-Activation Strategy Allylic Sulfination Xie, Peizhong Sun, Zuolian Li, Shuangshuang Cai, Xinying Qiu, Ju Fu, Weishan Gao, Cuiqing Wu, Shisheng Yang, Xiaobo Loh, Teck-Peng Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title | Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title_full | Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title_fullStr | Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title_full_unstemmed | Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title_short | Reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols |
| title_sort | reciprocal activation strategy for allylic sulfination with unactivated allylic alcohols |
| topic | Science::Chemistry Reciprocal-Activation Strategy Allylic Sulfination |
| url | https://hdl.handle.net/10356/155331 |
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