Synthesis of phenanthrenes through copper-catalyzed cross-Coupling of N-tosylhydrazones with terminal alkynes
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.
Hossain, Mohammad Lokman,Ye, Fei,Liu, Zhenxing,Xia, Ying,Shi, Yi,Zhou, Lei,Zhang, Yan,Wang, Jianbo
p. 8689 - 8699
(2015/01/08)
N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C
A mild and efficient method for the deoxygenative hydrogenation of aldehydes and ketones has been developed. The reaction is mediated by N-tosylhydrazine with H2 (1 atm) as the reductant and 10% Pd/C as the catalyst.
Expeditious synthesis of phenanthrenes via CuBr2-catalyzed coupling of terminal alkynes and N-tosylhydrazones derived from O-formyl biphenyls
A new method for the synthesis of phenanthrenes via ligand-free CuBr2-catalyzed coupling/cyclization of terminal alkynes with N-tosylhydrazones derived from o-formyl biphenyls has been developed. This new synthesis has wide range of functional group compatibility.
Ye, Fei,Shi, Yi,Zhou, Lei,Xiao, Qing,Zhang, Yan,Wang, Jianbo
p. 5020 - 5023
(2011/11/14)
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