Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant
Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol–ene...
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sg-ntu-dr.10356-820602023-02-28T19:28:55Z Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant Zhang, Yuexia Wong, Zeng Rong Wu, Xingxing Lauw, Sherman Jun Liang Huang, Xuan Webster, Richard David Chi, Yonggui Robin School of Physical and Mathematical Sciences Sulfoxides N-Fluorobenzenesulfonimide Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol–ene/–yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) Accepted version 2017-07-31T03:20:12Z 2019-12-06T14:45:41Z 2017-07-31T03:20:12Z 2019-12-06T14:45:41Z 2017 Journal Article Zhang, Y., Wong, Z. R., Wu, X., Lauw, S. J. L., Huang, X., Webster, R. D., et al. (2017). Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant. Chemical Communications, 53(1), 184-187. 1359-7345 https://hdl.handle.net/10356/82060 http://hdl.handle.net/10220/43495 10.1039/C6CC08631D en Chemical Communications © 2017 The Royal Society of Chemistry. This is the author created version of a work that has been peer reviewed and accepted for publication by Chemical Communications, The Royal Society of Chemistry. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1039/C6CC08631D]. 4 p. application/pdf |
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Sulfoxides N-Fluorobenzenesulfonimide |
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Sulfoxides N-Fluorobenzenesulfonimide Zhang, Yuexia Wong, Zeng Rong Wu, Xingxing Lauw, Sherman Jun Liang Huang, Xuan Webster, Richard David Chi, Yonggui Robin Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| description |
Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol–ene/–yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Zhang, Yuexia Wong, Zeng Rong Wu, Xingxing Lauw, Sherman Jun Liang Huang, Xuan Webster, Richard David Chi, Yonggui Robin |
| format |
Article |
| author |
Zhang, Yuexia Wong, Zeng Rong Wu, Xingxing Lauw, Sherman Jun Liang Huang, Xuan Webster, Richard David Chi, Yonggui Robin |
| author_sort |
Zhang, Yuexia |
| title |
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| title_short |
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| title_full |
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| title_fullStr |
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| title_full_unstemmed |
Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant |
| title_sort |
sulfoxidation of alkenes and alkynes with nfsi as a radical initiator and selective oxidant |
| publishDate |
2017 |
| url |
https://hdl.handle.net/10356/82060 http://hdl.handle.net/10220/43495 |
| _version_ |
1759853408874921984 |