92791-77-0Relevant academic research and scientific papers
NHC-Iridium-Catalyzed Deoxygenative Coupling of Primary Alcohols Producing Alkanes Directly: Synergistic Hydrogenation with Sodium Formate Generated in Situ
Lu, Zeye,Zheng, Qingshu,Yang, Siqi,Qian, Chun,Shen, Yajing,Tu, Tao
, p. 10796 - 10801 (2021/09/08)
The direct conversion of alcohols into long-chain alkanes is an attractive but extremely challenging approach for biomass upgrading. Here, we describe the highly selective deoxygenative coupling of aryl ethanols with primary alcohols to produce alkanes, using a bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complex as the catalyst. Up to quantitative yields and selectivity with a broad substrate scope are attained in both homo- and cross-coupling reactions. Mechanistic studies reveal that the further synergistic hydrogenation of the alkene intermediates by the formate generated in situ in the presence of bis-NHC-Ir is crucial for alkane production.
Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes
Yu, Fei,Wang, Ting,Zhou, Huan,Li, Yajun,Zhang, Xinhao,Bao, Hongli
supporting information, p. 6538 - 6541 (2017/12/26)
The untraditional iron-catalyzed, ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel-Crafts reaction. HOMO-LUMO analysis and DFT studies on the key transition states underlying the regioselectivity are consistent with the observed reactions and the conclusions.
Photochromism of 1,2-bis(2-n-alkyl-5-formyl-3-thienyl)perfluorocyclopentene derivatives
Pu, Shouzhi,Zhu, Shengsheng,Rao, Yi,Liu, Gang,Wei, Huizhen
experimental part, p. 89 - 100 (2009/08/15)
Photochromic diarylethene derivatives 1o-6o bearing long alkyl chains (≥seven carbon atoms) have been synthesized and their structures with the exception of compound 3o have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their properties, including photochromism both in solution and in PMMA film and their electrochemical properties were investigated in detail. All of these diarylethenes showed good photochromism both in solution and in PMMA film. The diarylethene derivatives with n-heptyl and n-octyl substituents at the 2-positions of the two thiophene rings exhibit photochromism even in the single-crystalline phase, but those with n-decyl, n-undecyl and n-dodecyl groups showed no photochromism in the single-crystalline phase. Compared to the photochromic features of 1,2-bis(2-methyl-5-formyl-3-thienyl)perfluorocyclopentene, introduction of the long alkyl groups was found to decrease the cycloreversion quantum yield and induce bathochromic shifts of the absorption spectra of the closed-ring isomers. The absorption coefficients of both open- and closed-ring isomers increased remarkably when replacing the methyl groups at 2-positions of the two thiophene rings with n-heptyl ones. However, further increase was not observed the alkyl chain becoming longer from n-heptyl to n-dodecyl groups. The cyclic voltammetry indicated that the HOMO and LUMO energy levels of these diarylethenes increased with the increase of the carbon numbers of alkyl chains from n-heptyl to n-dodecyl groups, but their band gaps were essentially not influenced by the alkyl chain length.
Unprecedented Negishi coupling at C-Br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis
Getmanenko, Yulia A.,Twieg, Robert J.
, p. 830 - 839 (2008/09/18)
(Chemical Equation Presented) The 2-bromo-5(or 6)-tri-n- butylstannylpyridines, prepared from dibromopyridines and i-PrMgCl at room temperature, undergo Negishi coupling with either alkyl or arylzinc chlorides. The new alkyl- and aryl-substituted pyridylstannanes produced are shown to be suitable for further functionalization by Stille coupling. A group of new liquid crystalline materials with aromatic cores comprised of pyridine and thiophene rings were prepared utilizing these new pyridinylstannanes as key intermediates.
