Feng Liu, Jia-Yin Wang, P. Zhou
Dec 4, 2017
Citations
1
Influential Citations
151
Citations
Quality indicators
Journal
Angewandte Chemie
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.