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

Research output: Contribution to journalArticlepeer-review

116 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 languageEnglish
Pages (from-to)15570-15574
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number49
DOIs
StatePublished - Dec 4 2017

Keywords

  • allenes
  • annulation
  • cycloaddition
  • diazo compounds
  • radicals

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