Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles

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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Main Authors: Wu, Junliang, Deng, Xiaozhou, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Alkynes
Cross-coupling
Online Access:https://hdl.handle.net/10356/144024
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.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
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Alkynes
Cross-coupling
spellingShingle Science::Chemistry
Alkynes
Cross-coupling
Wu, Junliang
Deng, Xiaozhou
Yoshikai, Naohiko
Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles
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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Wu, Junliang
Deng, Xiaozhou
Yoshikai, Naohiko
format Article
author Wu, Junliang
Deng, Xiaozhou
Yoshikai, Naohiko
author_sort Wu, Junliang
title Stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles
title_short 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_sort stereocontrolled synthesis of halovinylbenziodoxoles by hydro- and iodochlorination of ethynylbenziodoxoles
publishDate 2020
url https://hdl.handle.net/10356/144024
_version_ 1759854975820759040

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