Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles
We report herein the synthesis of highly substituted and stereochemically well‐defined vinylbenziodoxole (VBX) derivatives through hydrochlorination and iodochlorination of ethynylbenziodoxoles. The hydrochlorination is achieved using pyridine hydrochloride as an HCl source in an anti‐fashion under...
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| Format: | Journal Article |
| Language: | English |
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2020
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| Online Access: | https://hdl.handle.net/10356/144024 |
| _version_ | 1811685311847071744 |
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| author | Wu, Junliang Deng, Xiaozhou Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Wu, Junliang Deng, Xiaozhou Yoshikai, Naohiko |
| author_sort | Wu, Junliang |
| collection | NTU |
| description | We report herein the synthesis of highly substituted and stereochemically well‐defined vinylbenziodoxole (VBX) derivatives through hydrochlorination and iodochlorination of ethynylbenziodoxoles. The hydrochlorination is achieved using pyridine hydrochloride as an HCl source in an anti‐fashion under mild, open‐air conditions to afford a 2‐chlorinated VBX product, which serves as a useful building block for the stereoselective synthesis of trisubstituted alkenes. Meanwhile, iodochlorination with iodine monochloride proceeds in an unusual syn‐pathway, stereoselectively affording a tetrasubstituted VBX derivative. |
| first_indexed | 2024-10-01T04:42:31Z |
| format | Journal Article |
| id | ntu-10356/144024 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:42:31Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1440242023-02-28T19:48:16Z Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles Wu, Junliang Deng, Xiaozhou Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Alkynes Cross-coupling We report herein the synthesis of highly substituted and stereochemically well‐defined vinylbenziodoxole (VBX) derivatives through hydrochlorination and iodochlorination of ethynylbenziodoxoles. The hydrochlorination is achieved using pyridine hydrochloride as an HCl source in an anti‐fashion under mild, open‐air conditions to afford a 2‐chlorinated VBX product, which serves as a useful building block for the stereoselective synthesis of trisubstituted alkenes. Meanwhile, iodochlorination with iodine monochloride proceeds in an unusual syn‐pathway, stereoselectively affording a tetrasubstituted VBX derivative. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by the Ministry of Education (Singapore) and Nanyang Technological University (MOE2016-T2-2- 043). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis. 2020-10-08T06:29:51Z 2020-10-08T06:29:51Z 2019 Journal Article Wu, J., Deng, X., & Yoshikai, N. (2019). Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles. Chemistry – A European Journal, 25(33), 7839-7842. doi:10.1002/chem.201901543 0947-6539 https://hdl.handle.net/10356/144024 10.1002/chem.201901543 31020740 33 25 7839 7842 en Chemistry – A European Journal This is the accepted version of the following article: Wu, J., Deng, X., & Yoshikai, N. (2019). Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles. Chemistry – A European Journal, 25(33), 7839-7842. doi:10.1002/chem.201901543, which has been published in final form at http://doi.org/10.1002/chem.201901543. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf |
| spellingShingle | Science::Chemistry Alkynes Cross-coupling Wu, Junliang Deng, Xiaozhou Yoshikai, Naohiko Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title | Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title_full | Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title_fullStr | Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title_full_unstemmed | Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title_short | Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles |
| title_sort | stereocontrolled synthesis of halovinylbenziodoxoles by hydro and iodochlorination of ethynylbenziodoxoles |
| topic | Science::Chemistry Alkynes Cross-coupling |
| url | https://hdl.handle.net/10356/144024 |
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