Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates
An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp )−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for p...
| Main Authors: | , , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2021
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| Online Access: | https://hdl.handle.net/10356/147428 |
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| author | Zhu, Tong-Hao Zhang, Xiao-Chen Cui, Xian-Lu Zhang, Ze-Yu Jiang, Hui Sun, Shan-Shan Zhao, Li-Li Zhao, Kai Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhu, Tong-Hao Zhang, Xiao-Chen Cui, Xian-Lu Zhang, Ze-Yu Jiang, Hui Sun, Shan-Shan Zhao, Li-Li Zhao, Kai Loh, Teck-Peng |
| author_sort | Zhu, Tong-Hao |
| collection | NTU |
| description | An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp )−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. |
| first_indexed | 2024-10-01T04:11:24Z |
| format | Journal Article |
| id | ntu-10356/147428 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:11:24Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1474282021-04-01T00:56:37Z Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates Zhu, Tong-Hao Zhang, Xiao-Chen Cui, Xian-Lu Zhang, Ze-Yu Jiang, Hui Sun, Shan-Shan Zhao, Li-Li Zhao, Kai Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Organic Catalysis C-H Functionalization An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp )−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. We gratefully acknowledge the financial support from NanjingTech University (Start-up Grant No. 39837137, 39837101 and3827401739), and National Natural Science Foundation ofChina (21372210, 21672198, 21801129), the State Key Pro-gram of National Natural Science Foundation of China(21432009), Natural science research projects in Jiangsuhigher education institutions (18KJB150018) for generousfinancial support. 2021-04-01T00:56:37Z 2021-04-01T00:56:37Z 2019 Journal Article Zhu, T., Zhang, X., Cui, X., Zhang, Z., Jiang, H., Sun, S., Zhao, L., Zhao, K. & Loh, T. (2019). Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates. Advanced Synthesis & Catalysis, 361(15), 3593-3598. https://dx.doi.org/10.1002/adsc.201900257 1615-4150 https://hdl.handle.net/10356/147428 10.1002/adsc.201900257 2-s2.0-85065966208 15 361 3593 3598 en Advanced Synthesis & Catalysis © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved. |
| spellingShingle | Science::Chemistry Organic Catalysis C-H Functionalization Zhu, Tong-Hao Zhang, Xiao-Chen Cui, Xian-Lu Zhang, Ze-Yu Jiang, Hui Sun, Shan-Shan Zhao, Li-Li Zhao, Kai Loh, Teck-Peng Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title | Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title_full | Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title_fullStr | Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title_full_unstemmed | Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title_short | Direct C(sp2)-H arylsulfonylation of enamides via iridium(III)-catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| title_sort | direct c sp2 h arylsulfonylation of enamides via iridium iii catalyzed insertion of sulfur dioxide with aryldiazonium tetrafluoroborates |
| topic | Science::Chemistry Organic Catalysis C-H Functionalization |
| url | https://hdl.handle.net/10356/147428 |
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