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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Detalles Bibliográficos
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
Descripción
Sumario:[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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