Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols
The transition-metal free S-vinylation of thiophenols by vinylbenziodoxolones (VBX) constituted an important step forward in hypervalent iodine-mediated vinylations, highlighting the difference to vinyliodonium salts and that the reaction outcome was influenced by the substitution pattern of the ben...
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Frontiers Media S.A.
2024-02-01
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Series: | Frontiers in Chemistry |
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Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2024.1376948/full |
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author | Sayad Doobary Ester Maria Di Tommaso Alexandru Postole A. Ken Inge Berit Olofsson |
author_facet | Sayad Doobary Ester Maria Di Tommaso Alexandru Postole A. Ken Inge Berit Olofsson |
author_sort | Sayad Doobary |
collection | DOAJ |
description | The transition-metal free S-vinylation of thiophenols by vinylbenziodoxolones (VBX) constituted an important step forward in hypervalent iodine-mediated vinylations, highlighting the difference to vinyliodonium salts and that the reaction outcome was influenced by the substitution pattern of the benziodoxolone core. In this study, we report several new classes of hypervalent iodine vinylation reagents; vinylbenziodazolones, vinylbenziodoxolonimine and vinyliodoxathiole dioxides. Their synthesis, structural and electronic properties are described and correlated to the S-vinylation outcome, shedding light on some interesting facets of these reagents. |
first_indexed | 2024-03-07T19:44:03Z |
format | Article |
id | doaj.art-ff491f0ed8244789bd76751b61fa5277 |
institution | Directory Open Access Journal |
issn | 2296-2646 |
language | English |
last_indexed | 2024-03-07T19:44:03Z |
publishDate | 2024-02-01 |
publisher | Frontiers Media S.A. |
record_format | Article |
series | Frontiers in Chemistry |
spelling | doaj.art-ff491f0ed8244789bd76751b61fa52772024-02-29T04:53:19ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462024-02-011210.3389/fchem.2024.13769481376948Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiolsSayad Doobary0Ester Maria Di Tommaso1Alexandru Postole2A. Ken Inge3Berit Olofsson4Department of Organic Chemistry, Stockholm University, Stockholm, SwedenDepartment of Organic Chemistry, Stockholm University, Stockholm, SwedenDepartment of Organic Chemistry, Stockholm University, Stockholm, SwedenDepartment of Materials and Environmental Chemistry, Stockholm University, Stockholm, SwedenDepartment of Organic Chemistry, Stockholm University, Stockholm, SwedenThe transition-metal free S-vinylation of thiophenols by vinylbenziodoxolones (VBX) constituted an important step forward in hypervalent iodine-mediated vinylations, highlighting the difference to vinyliodonium salts and that the reaction outcome was influenced by the substitution pattern of the benziodoxolone core. In this study, we report several new classes of hypervalent iodine vinylation reagents; vinylbenziodazolones, vinylbenziodoxolonimine and vinyliodoxathiole dioxides. Their synthesis, structural and electronic properties are described and correlated to the S-vinylation outcome, shedding light on some interesting facets of these reagents.https://www.frontiersin.org/articles/10.3389/fchem.2024.1376948/fullalkenesbenziodoxoloneshypervalencyreduction potentialX-ray crystallographystructure-reactivity analysis |
spellingShingle | Sayad Doobary Ester Maria Di Tommaso Alexandru Postole A. Ken Inge Berit Olofsson Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols Frontiers in Chemistry alkenes benziodoxolones hypervalency reduction potential X-ray crystallography structure-reactivity analysis |
title | Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols |
title_full | Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols |
title_fullStr | Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols |
title_full_unstemmed | Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols |
title_short | Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols |
title_sort | structure reactivity analysis of novel hypervalent iodine reagents in s vinylation of thiols |
topic | alkenes benziodoxolones hypervalency reduction potential X-ray crystallography structure-reactivity analysis |
url | https://www.frontiersin.org/articles/10.3389/fchem.2024.1376948/full |
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