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Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols

Authors :
Sayad Doobary
Ester Maria Di Tommaso
Alexandru Postole
A. Ken Inge
Berit Olofsson
Source :
Frontiers in Chemistry, Vol 12 (2024)
Publication Year :
2024
Publisher :
Frontiers Media S.A., 2024.

Abstract

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.

Details

Language :
English
ISSN :
22962646
Volume :
12
Database :
Directory of Open Access Journals
Journal :
Frontiers in Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.ff491f0ed8244789bd76751b61fa5277
Document Type :
article
Full Text :
https://doi.org/10.3389/fchem.2024.1376948