916588-75-5Relevant academic research and scientific papers
Synthesis of phenanthrenes through copper-catalyzed cross-Coupling of N-tosylhydrazones with terminal alkynes
Hossain, Mohammad Lokman,Ye, Fei,Liu, Zhenxing,Xia, Ying,Shi, Yi,Zhou, Lei,Zhang, Yan,Wang, Jianbo
, p. 8689 - 8699 (2015/01/08)
A novel protocol for the synthesis of phenanthrenes through the copper-catalyzed reaction of aromatic tosylhydrazones with terminal alkynes is explored. The reaction proceeds via the formation of an allene intermediate and subsequent six-π-electron cyclization-isomerization, affording phenanthrene derivatives in good yields. The transformation can be performed in two ways:(1)with Ntosylhydrazones derived from [1,1'-biphenyl]-2-carbaldehydes and terminal alkynes as the starting materials and(2)with Ntosylhydrazones derived from aromatic aldehydes and 2-alkynyl biphenyls as the starting materials. This new phenanthrene synthesis uses readily available starting materials and a cheap copper catalyst and has a wide range of functional group compatibility.
Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes and evidence for an allene intermediate in the novel base-catalyzed cyclization of 2-alkynylbiphenyls
Wang, Yi,Burton, Donald J.
, p. 5295 - 5298 (2007/10/03)
A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.
