Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions

[Image: see text] For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft–soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine...

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Autores principales: Kim, Sang Mee, Kang, On-Yu, Lim, Hwan Jung, Park, Seong Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7203956/
https://www.ncbi.nlm.nih.gov/pubmed/32391507
http://dx.doi.org/10.1021/acsomega.0c01086
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author Kim, Sang Mee
Kang, On-Yu
Lim, Hwan Jung
Park, Seong Jun
author_facet Kim, Sang Mee
Kang, On-Yu
Lim, Hwan Jung
Park, Seong Jun
author_sort Kim, Sang Mee
collection PubMed
description [Image: see text] For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft–soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine (III) diacetate (PIDA) in N,N-dimethylformamide (DMF). The sulfur imination reactions were tolerant to a wide range of functional groups and exhibited high selectivities and excellent yields. The existence of thionium ion intermediates was confirmed by ultraviolet/visible (UV/vis) spectroscopy and (1)H NMR experiments.
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spelling pubmed-72039562020-05-08 Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions Kim, Sang Mee Kang, On-Yu Lim, Hwan Jung Park, Seong Jun ACS Omega [Image: see text] For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft–soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine (III) diacetate (PIDA) in N,N-dimethylformamide (DMF). The sulfur imination reactions were tolerant to a wide range of functional groups and exhibited high selectivities and excellent yields. The existence of thionium ion intermediates was confirmed by ultraviolet/visible (UV/vis) spectroscopy and (1)H NMR experiments. American Chemical Society 2020-04-22 /pmc/articles/PMC7203956/ /pubmed/32391507 http://dx.doi.org/10.1021/acsomega.0c01086 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kim, Sang Mee
Kang, On-Yu
Lim, Hwan Jung
Park, Seong Jun
Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title_full Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title_fullStr Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title_full_unstemmed Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title_short Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
title_sort selective synthesis of n-cyano sulfilimines by dearomatizing stable thionium ions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7203956/
https://www.ncbi.nlm.nih.gov/pubmed/32391507
http://dx.doi.org/10.1021/acsomega.0c01086
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AT limhwanjung selectivesynthesisofncyanosulfiliminesbydearomatizingstablethioniumions
AT parkseongjun selectivesynthesisofncyanosulfiliminesbydearomatizingstablethioniumions

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