We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[ a]naphthalen-4-ols.
- Authors
Liu, Feng; Wang, Jia‐Yin; Zhou, Peng; Li, Guigen; Hao, Wen‐Juan; Tu, Shu‐Jiang; Jiang, Bo
- 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.
- Subjects
RING formation (Chemistry); RADICALS (Chemistry); ADDITION reactions; NAPHTHOL; BENZENE
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 49, p15776
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201707615