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One-pot synthesis of N-iodo sulfoximines from sulfides
ID
Zupanc, Anže
(
Author
),
ID
Jereb, Marjan
(
Author
)
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https://pubs.acs.org/doi/10.1021/acs.joc.1c00292
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Abstract
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF$_3$ congeners have been demonstrated.
Language:
English
Keywords:
sulfides
,
sulfoximines
,
one-pot
,
N-iodo sulfoximines
,
chemical reactions
,
isolation
,
mixtures
,
nuclear magnetic resonance spectroscopy
Work type:
Article
Typology:
1.01 - Original Scientific Article
Organization:
FKKT - Faculty of Chemistry and Chemical Technology
Publication status:
Published
Publication version:
Version of Record
Year:
2021
Number of pages:
Str. 5991-6000
Numbering:
Vol. 86, iss. 8
PID:
20.500.12556/RUL-127256
UDC:
547.544
ISSN on article:
0022-3263
DOI:
10.1021/acs.joc.1c00292
COBISS.SI-ID:
58059779
Publication date in RUL:
31.05.2021
Views:
854
Downloads:
312
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Record is a part of a journal
Title:
Journal of organic chemistry
Shortened title:
J. org. chem.
Publisher:
American Chemical Society
ISSN:
0022-3263
COBISS.SI-ID:
235287
Licences
License:
CC BY 4.0, Creative Commons Attribution 4.0 International
Link:
http://creativecommons.org/licenses/by/4.0/
Description:
This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
Secondary language
Language:
Slovenian
Keywords:
sulfidi
,
sulfoksimini
,
enolončna pretvorba
,
N-jodo sulfoksimini
Projects
Funder:
ARRS - Slovenian Research Agency
Project number:
P1-0230
Name:
Organska kemija: sinteza, struktura in aplikacija
Funder:
ARRS - Slovenian Research Agency
Funding programme:
Young researchers
Funder:
ARRS - Slovenian Research Agency
Project number:
J1-8147
Name:
Ligandi s tzNHC strukturo v organokovinski kemiji in homogeni katalizi: tvorba vezi C-C in C-N v vodi
Funder:
ARRS - Slovenian Research Agency
Project number:
J1-9166
Name:
Redefinicija in razširitev uporabe Sonogashirove reakcije pripajanja brez bakra
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