Direct C(sp2)-H Arylsulfonylation of Enamides via Iridium(III)-Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates

Tong Hao Zhu; Xiao Chen Zhang; Xian Lu Cui; Ze Yu Zhang; Hui Jiang; Shan Shan Sun; Li Li Zhao; Kai Zhao; Teck Peng Loh

doi:10.1002/adsc.201900257

Direct C(sp²)-H Arylsulfonylation of Enamides via Iridium(III)-Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates

Tong Hao Zhu, Xiao Chen Zhang, Xian Lu Cui, Ze Yu Zhang, Hui Jiang, Shan Shan Sun, Li Li Zhao, Kai Zhao^*, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

76 Citations (Scopus)

Abstract

An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp²)−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. (Figure presented.).

Original language	English
Pages (from-to)	3593-3598
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	361
Issue number	15
DOIs	https://doi.org/10.1002/adsc.201900257
Publication status	Published - Aug 5 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

C−H functionalization
Enamides
Insertion of sulfur dioxide
Organic catalysis
β-Amido sulfones

Access to Document

10.1002/adsc.201900257

Cite this

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title = "Direct C(sp2)-H Arylsulfonylation of Enamides via Iridium(III)-Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates",

abstract = "An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp2)−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. (Figure presented.).",

keywords = "C−H functionalization, Enamides, Insertion of sulfur dioxide, Organic catalysis, β-Amido sulfones",

author = "Zhu, \{Tong Hao\} and Zhang, \{Xiao Chen\} and Cui, \{Xian Lu\} and Zhang, \{Ze Yu\} and Hui Jiang and Sun, \{Shan Shan\} and Zhao, \{Li Li\} and Kai Zhao and Loh, \{Teck Peng\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = aug,

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doi = "10.1002/adsc.201900257",

language = "English",

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journal = "Advanced Synthesis and Catalysis",

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T1 - Direct C(sp2)-H Arylsulfonylation of Enamides via Iridium(III)-Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates

AU - Zhu, Tong Hao

AU - Zhang, Xiao Chen

AU - Cui, Xian Lu

AU - Zhang, Ze Yu

AU - Jiang, Hui

AU - Sun, Shan Shan

AU - Zhao, Li Li

AU - Zhao, Kai

AU - Loh, Teck Peng

PY - 2019/8/5

Y1 - 2019/8/5

N2 - An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp2)−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. (Figure presented.).

AB - An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp2)−H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of β-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance. (Figure presented.).

KW - C−H functionalization

KW - Enamides

KW - Insertion of sulfur dioxide

KW - Organic catalysis

KW - β-Amido sulfones

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