Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols

Feng Liu; Jia Yin Wang; Peng Zhou; Guigen Li; Wen Juan Hao; Shu Jiang Tu; Bo Jiang

doi:10.1002/anie.201707615

Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols

Feng Liu, Jia Yin Wang, Peng Zhou, Guigen Li, Wen Juan Hao, Shu Jiang Tu, Bo Jiang

Chemistry and Biochemistry

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

116 Scopus citations

Abstract

A metal-free [2+2] cycloaddition and 1,4-addition sequence induced by S-centered radicals has been achieved by treating benzene-linked allene-ynes with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) in a one-pot procedure. The reaction provides a greener and more practical access to functionalized cyclobuta[a]naphthalen-4-ols with valuable applications. More than 50 examples are demonstrated with excellent diastereoselectivity and chemical yields. The reaction pathway is proposed to proceed by the following steps:[2+2] cycloaddition, insertion of SO₂, 1,4-addition, diazotization, and tautomerization.

Original language	English
Pages (from-to)	15570-15574
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	49
DOIs	https://doi.org/10.1002/anie.201707615
State	Published - Dec 4 2017

Keywords

allenes
annulation
cycloaddition
diazo compounds
radicals

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10.1002/anie.201707615

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@article{f45e252140f441e09a33fdb66747dcea,

title = "Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols",

abstract = "A metal-free [2+2] cycloaddition and 1,4-addition sequence induced by S-centered radicals has been achieved by treating benzene-linked allene-ynes with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) in a one-pot procedure. The reaction provides a greener and more practical access to functionalized cyclobuta[a]naphthalen-4-ols with valuable applications. More than 50 examples are demonstrated with excellent diastereoselectivity and chemical yields. The reaction pathway is proposed to proceed by the following steps:[2+2] cycloaddition, insertion of SO2, 1,4-addition, diazotization, and tautomerization.",

keywords = "allenes, annulation, cycloaddition, diazo compounds, radicals",

author = "Feng Liu and Wang, {Jia Yin} and Peng Zhou and Guigen Li and Hao, {Wen Juan} and Tu, {Shu Jiang} and Bo Jiang",

year = "2017",

month = dec,

day = "4",

doi = "10.1002/anie.201707615",

language = "English",

volume = "56",

pages = "15570--15574",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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}

Merging [2+2] Cycloaddition with Radical 1,4-Addition : Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols. / Liu, Feng; Wang, Jia Yin; Zhou, Peng; Li, Guigen; Hao, Wen Juan; Tu, Shu Jiang; Jiang, Bo.

In: Angewandte Chemie - International Edition, Vol. 56, No. 49, 04.12.2017, p. 15570-15574.

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

TY - JOUR

T1 - Merging [2+2] Cycloaddition with Radical 1,4-Addition

T2 - Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols

AU - Liu, Feng

AU - Wang, Jia Yin

AU - Zhou, Peng

AU - Li, Guigen

AU - Hao, Wen Juan

AU - Tu, Shu Jiang

AU - Jiang, Bo

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AB - A metal-free [2+2] cycloaddition and 1,4-addition sequence induced by S-centered radicals has been achieved by treating benzene-linked allene-ynes with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) in a one-pot procedure. The reaction provides a greener and more practical access to functionalized cyclobuta[a]naphthalen-4-ols with valuable applications. More than 50 examples are demonstrated with excellent diastereoselectivity and chemical yields. The reaction pathway is proposed to proceed by the following steps:[2+2] cycloaddition, insertion of SO2, 1,4-addition, diazotization, and tautomerization.

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KW - radicals

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