84648-90-8Relevant academic research and scientific papers
Transition-metal-free intramolecular carbene aromatic substitution/Büchner reaction: Synthesis of fluorenes and [6,5,7]benzo-fused rings
Liu, Zhenxing,Tan, Haocheng,Wang, Long,Fu, Tianren,Xia, Ying,Zhang, Yan,Wang, Jianbo
supporting information, p. 3056 - 3060 (2015/03/30)
Intramolecular aromatic substitution and Büchner reaction have been established as powerful methods for the construction of polycyclic compounds. These reactions are traditionally catalyzed by RhII catalysts with a-diazocarbonyl compounds as the substrates. Herein a transition-metal-free intramolecular aromatic substitution/Büchner reaction is presented. These reactions use readily available N-tosylhydrazones as the diazo compound precursors and show wide substrate scope.
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.
N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C
Zhou, Lei,Liu, Zhenxing,Liu, Yizhou,Zhang, Yan,Wang, Jianbo
, p. 6083 - 6087 (2013/07/25)
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.
C(sp)-C(sp3) bond formation through cu-catalyzed cross-coupling of N -tosylhydrazones and trialkylsilylethynes
Ye, Fei,Ma, Xiaoshen,Xiao, Qing,Li, Huan,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 5742 - 5745 (2012/05/07)
Copper-catalyzed cross-coupling of N-tosylhydrazones with trialkylsilylethynes leads to the formation of C(sp)-C(sp3) bonds. Cu carbene migratory insertion is proposed to play the key role in this transformation.
Expeditious synthesis of phenanthrenes via CuBr2-catalyzed coupling of terminal alkynes and N-tosylhydrazones derived from O-formyl biphenyls
Ye, Fei,Shi, Yi,Zhou, Lei,Xiao, Qing,Zhang, Yan,Wang, Jianbo
, p. 5020 - 5023 (2011/11/14)
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.
Solid-State Chemistry, Kinetics, and Electron Spin Resonance Spectroscopy of 2-Biphenylmethylene
Palik, Eric C.,Platz, Matthew S.
, p. 963 - 969 (2007/10/02)
The chemistry and kinetics of 2-biphenylmethylene have been examined in low-temperature glasses and polycrystals.Photolysis of 2-biphenyldiazomethane at 77 K produces a single set of triplet carbene resonance peaks.They have been assigned to the unresolved superposition of syn and anti rotamers of the carbene.The carbene kinetics are fastest in diethyl ether glass.The decay rates of 4T in diethyl-d10 ether and in a perfluorinated alkane polycrystal are comparable.This indicated that the main carbene reaction in diethyl ether is hydrogen atom abstraction.The reaction of 4T in diethyl-d10 ether is a mixture of reaction with solvent and cyclization to fluorene.These interpretations are consistent with the observed product distributions.Matrix effects on the observed chemistry are discussed.
