One-Pot Manganese (IV)-Mediated Synthesis of Sulfonyl Fluorides from Arylhydrazines

Van Hieu Tran; Hee Kwon Kim

doi:10.1002/ajoc.202200004

One-Pot Manganese (IV)-Mediated Synthesis of Sulfonyl Fluorides from Arylhydrazines

Van Hieu Tran
, Hee Kwon Kim^*

^*Corresponding author for this work

Department of Medicine

Jeonbuk National University

Research output: Contribution to journal › Journal article › peer-review

3 Scopus citations

Abstract

Sulfonyl fluorides, a useful structure in various organic syntheses, are found in several biologically active molecules and have been used in sulfur (VI) fluoride exchange-based “click chemistry”. In the present study, a novel MnO₂-mediated synthetic method to prepare sulfonyl fluorides from aryl hydrazines employing DABSO and NFSI as effective reagents affording a variety of sulfonyl fluoride products in good to excellent yields is described. Our results suggest the generality of this MnO₂ mediated transformation of various aryl hydrazines into sulfonyl fluorides under mild reaction conditions.

Original language	English
Article number	e202200004
Journal	Asian Journal of Organic Chemistry
Volume	11
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.202200004
State	Published - 2022.04

Keywords

Arylhydrazines
Fluorinating agent
Manganese (IV) oxide
Sulfonyl fluorides
Sulfur dioxide surrogate

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Chemistry

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10.1002/ajoc.202200004

Cite this

@article{ed0e16946b2247ceb260cd06b37fcf9e,

title = "One-Pot Manganese (IV)-Mediated Synthesis of Sulfonyl Fluorides from Arylhydrazines",

abstract = "Sulfonyl fluorides, a useful structure in various organic syntheses, are found in several biologically active molecules and have been used in sulfur (VI) fluoride exchange-based “click chemistry”. In the present study, a novel MnO2-mediated synthetic method to prepare sulfonyl fluorides from aryl hydrazines employing DABSO and NFSI as effective reagents affording a variety of sulfonyl fluoride products in good to excellent yields is described. Our results suggest the generality of this MnO2 mediated transformation of various aryl hydrazines into sulfonyl fluorides under mild reaction conditions.",

keywords = "Arylhydrazines, Fluorinating agent, Manganese (IV) oxide, Sulfonyl fluorides, Sulfur dioxide surrogate",

author = "Tran, \{Van Hieu\} and Kim, \{Hee Kwon\}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = apr,

doi = "10.1002/ajoc.202200004",

language = "English",

volume = "11",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

number = "4",

}

TY - JOUR

T1 - One-Pot Manganese (IV)-Mediated Synthesis of Sulfonyl Fluorides from Arylhydrazines

AU - Tran, Van Hieu

AU - Kim, Hee Kwon

PY - 2022/4

Y1 - 2022/4

N2 - Sulfonyl fluorides, a useful structure in various organic syntheses, are found in several biologically active molecules and have been used in sulfur (VI) fluoride exchange-based “click chemistry”. In the present study, a novel MnO2-mediated synthetic method to prepare sulfonyl fluorides from aryl hydrazines employing DABSO and NFSI as effective reagents affording a variety of sulfonyl fluoride products in good to excellent yields is described. Our results suggest the generality of this MnO2 mediated transformation of various aryl hydrazines into sulfonyl fluorides under mild reaction conditions.

AB - Sulfonyl fluorides, a useful structure in various organic syntheses, are found in several biologically active molecules and have been used in sulfur (VI) fluoride exchange-based “click chemistry”. In the present study, a novel MnO2-mediated synthetic method to prepare sulfonyl fluorides from aryl hydrazines employing DABSO and NFSI as effective reagents affording a variety of sulfonyl fluoride products in good to excellent yields is described. Our results suggest the generality of this MnO2 mediated transformation of various aryl hydrazines into sulfonyl fluorides under mild reaction conditions.

KW - Arylhydrazines

KW - Fluorinating agent

KW - Manganese (IV) oxide

KW - Sulfonyl fluorides

KW - Sulfur dioxide surrogate

UR - https://www.scopus.com/pages/publications/85124818798

U2 - 10.1002/ajoc.202200004

DO - 10.1002/ajoc.202200004

M3 - Journal article

AN - SCOPUS:85124818798

SN - 2193-5807

VL - 11

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 4

M1 - e202200004

ER -

One-Pot Manganese (IV)-Mediated Synthesis of Sulfonyl Fluorides from Arylhydrazines

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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