Double SO2 Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides

Ai Fang Wang; Wen Juan Hao; Yi Long Zhu; Guigen Li; Peng Zhou; Shu Jiang Tu; Bo Jiang

doi:10.1021/acsomega.7b01789

Double SO₂ Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides

Ai Fang Wang, Wen Juan Hao, Yi Long Zhu, Guigen Li, Peng Zhou, Shu Jiang Tu, Bo Jiang

Chemistry and Biochemistry

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

37 Scopus citations

Abstract

A novel metal-free double SO₂ insertion/multicomponent bicyclization cascade of benzene-linked 1,7-diynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under redox-neutral conditions, providing a range of dual sulfone-containing naphtho[1,2-c]thiophene 2,2-dioxides with generally high stereoselectivity. The reaction pathway is proposed to proceed through the sequence of arylsulfonyl-radical-induced 6-exo-dig/5-endo-trig bicyclization, H-abstraction, and diazotization.

Original language	English
Pages (from-to)	1482-1491
Number of pages	10
Journal	ACS Omega
Volume	3
Issue number	2
DOIs	https://doi.org/10.1021/acsomega.7b01789
State	Published - Feb 28 2018

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abstract = "A novel metal-free double SO2 insertion/multicomponent bicyclization cascade of benzene-linked 1,7-diynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under redox-neutral conditions, providing a range of dual sulfone-containing naphtho[1,2-c]thiophene 2,2-dioxides with generally high stereoselectivity. The reaction pathway is proposed to proceed through the sequence of arylsulfonyl-radical-induced 6-exo-dig/5-endo-trig bicyclization, H-abstraction, and diazotization.",

author = "Wang, {Ai Fang} and Hao, {Wen Juan} and Zhu, {Yi Long} and Guigen Li and Peng Zhou and Tu, {Shu Jiang} and Bo Jiang",

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AU - Wang, Ai Fang

AU - Hao, Wen Juan

AU - Zhu, Yi Long

AU - Li, Guigen

AU - Zhou, Peng

AU - Tu, Shu Jiang

AU - Jiang, Bo

PY - 2018/2/28

Y1 - 2018/2/28

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AB - A novel metal-free double SO2 insertion/multicomponent bicyclization cascade of benzene-linked 1,7-diynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under redox-neutral conditions, providing a range of dual sulfone-containing naphtho[1,2-c]thiophene 2,2-dioxides with generally high stereoselectivity. The reaction pathway is proposed to proceed through the sequence of arylsulfonyl-radical-induced 6-exo-dig/5-endo-trig bicyclization, H-abstraction, and diazotization.

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Double SO₂ Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides

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