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

[Image: see text] A novel metal-free double SO(2) 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-contai...

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Autores principales: Wang, Ai-Fang, Hao, Wen-Juan, Zhu, Yi-Long, Li, Guigen, Zhou, Peng, Tu, Shu-Jiang, Jiang, Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641491/
https://www.ncbi.nlm.nih.gov/pubmed/31458474
http://dx.doi.org/10.1021/acsomega.7b01789
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author Wang, Ai-Fang
Hao, Wen-Juan
Zhu, Yi-Long
Li, Guigen
Zhou, Peng
Tu, Shu-Jiang
Jiang, Bo
author_facet Wang, Ai-Fang
Hao, Wen-Juan
Zhu, Yi-Long
Li, Guigen
Zhou, Peng
Tu, Shu-Jiang
Jiang, Bo
author_sort Wang, Ai-Fang
collection PubMed
description [Image: see text] A novel metal-free double SO(2) 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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spelling pubmed-66414912019-08-27 Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides Wang, Ai-Fang Hao, Wen-Juan Zhu, Yi-Long Li, Guigen Zhou, Peng Tu, Shu-Jiang Jiang, Bo ACS Omega [Image: see text] A novel metal-free double SO(2) 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. American Chemical Society 2018-02-05 /pmc/articles/PMC6641491/ /pubmed/31458474 http://dx.doi.org/10.1021/acsomega.7b01789 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Wang, Ai-Fang
Hao, Wen-Juan
Zhu, Yi-Long
Li, Guigen
Zhou, Peng
Tu, Shu-Jiang
Jiang, Bo
Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title_full Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title_fullStr Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title_full_unstemmed Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title_short Double SO(2) Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides
title_sort double so(2) insertion into 1,7-diynes leading to functionalized naphtho[1,2-c]thiophene 2,2-dioxides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641491/
https://www.ncbi.nlm.nih.gov/pubmed/31458474
http://dx.doi.org/10.1021/acsomega.7b01789
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