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

Research output: Contribution to journalArticle

29 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 languageEnglish
Pages (from-to)1482-1491
Number of pages10
JournalACS Omega
Volume3
Issue number2
DOIs
StatePublished - Feb 28 2018

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