Cu(OTf)2-mediated C(sp2)-H arylsulfonylation of enamides via the insertion of sulfur dioxide

Tong Hao Zhu; Xiao Chen Zhang; Kai Zhao; Teck Peng Loh

doi:10.1039/c8qo01144c

Cu(OTf)₂-mediated C(sp²)-H arylsulfonylation of enamides via the insertion of sulfur dioxide

Tong Hao Zhu, Xiao Chen Zhang, Kai Zhao, Teck Peng Loh

School of Chemistry and Moleculai Engineering

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

79 Scopus citations

Abstract

An efficient and straightforward 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 has been developed. This Cu(OTf)₂-mediated SO₂ insertion reaction proceeds smoothly to afford a diverse range of β-amidovinyl sulfones bearing manifold functional groups in moderate to excellent yields with high regio- and stereoselectivities.

Original language	English
Pages (from-to)	94-98
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	1
DOIs	https://doi.org/10.1039/c8qo01144c
State	Published - 7 Jan 2019

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title = "Cu(OTf)2-mediated C(sp2)-H arylsulfonylation of enamides via the insertion of sulfur dioxide",

abstract = "An efficient and straightforward 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 has been developed. This Cu(OTf)2-mediated SO2 insertion reaction proceeds smoothly to afford a diverse range of β-amidovinyl sulfones bearing manifold functional groups in moderate to excellent yields with high regio- and stereoselectivities.",

author = "Zhu, {Tong Hao} and Zhang, {Xiao Chen} and Kai Zhao and Loh, {Teck Peng}",

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AU - Zhao, Kai

AU - Loh, Teck Peng

PY - 2019/1/7

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AB - An efficient and straightforward 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 has been developed. This Cu(OTf)2-mediated SO2 insertion reaction proceeds smoothly to afford a diverse range of β-amidovinyl sulfones bearing manifold functional groups in moderate to excellent yields with high regio- and stereoselectivities.

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Cu(OTf)₂-mediated C(sp²)-H arylsulfonylation of enamides via the insertion of sulfur dioxide

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