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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Main Authors: Sayad Doobary, Ester Maria Di Tommaso, Alexandru Postole, A. Ken Inge, Berit Olofsson
Format: Article
Language:English
Published: Frontiers Media S.A. 2024-02-01
Series:Frontiers in Chemistry
Subjects:
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.
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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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