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

130 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",

note = "Funding Information: We are grateful for financial support from the NSFC (Nos. 21332005, 21232004, and 21472071), PAPD of Jiangsu Higher Education Institutions, the Outstanding Youth Fund of JSNU (YQ2015003), NSF of Jiangsu Province (BK20151163), Robert A. Welch Foundation (D-1361, USA), and the Texas Tech University research promotion fund (to BJ). Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = dec,

day = "4",

doi = "10.1002/anie.201707615",

language = "English",

volume = "56",

pages = "15570--15574",

journal = "Angewandte Chemie - International Edition",

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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

N1 - Funding Information: We are grateful for financial support from the NSFC (Nos. 21332005, 21232004, and 21472071), PAPD of Jiangsu Higher Education Institutions, the Outstanding Youth Fund of JSNU (YQ2015003), NSF of Jiangsu Province (BK20151163), Robert A. Welch Foundation (D-1361, USA), and the Texas Tech University research promotion fund (to BJ). Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/12/4

Y1 - 2017/12/4

N2 - 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.

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.

KW - allenes

KW - annulation

KW - cycloaddition

KW - diazo compounds

KW - radicals

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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IS - 49

ER -

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

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