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Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations
Journal of Organometallic Chemistry ( IF 2.1 ) Pub Date : 2020-11-26 , DOI: 10.1016/j.jorganchem.2020.121626
Manoj Kumar Gangwar , Ray J. Butcher

Herein, we report the novel axially chiral bis-Ag(I)-MIC and, bis-Au(I)-MIC complexes bearing axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands were synthesized. The enantiopure R-BINOL was employed as a basic unit to synthesize a axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a. In particular, the axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a, were obtained from the reaction of corresponding bis-1,2,3-triazole ligand precursor with methyl and ethyl iodide in 82−90% yields. Novel axially chiral bis-Ag(I)-MIC complexes (1  2)b, were prepared by the treatment of corresponding axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) iodide salts, (1  2)a, with Ag2O via in-situ deprotonation method in 69−86% yields. Novel axially chiral bis-Au(I)-MIC complex-2c was synthesized from their respective novel axially chiral bis-Ag(I)-MIC complex-2b, using transmetallation reaction with (SMe2)AuCl in 70% yield. All these novel axially chiral bis-Ag(I)-MIC and bis-Au(I)-MIC complexes were isolated for the first time and structurally characterized by 1H NMR and 13C{1H}-NMR spectroscopy, FT-IR spectroscopy, mass spectrometry, elemental analysis, specific optical rotation and, single crystal X-ray crystallography.



中文翻译:

R)-BINOL和(-)-薄荷醇骨架的轴向手性双-1,2,3-三唑-4-亚烷基-Ag(I)-MIC和bis-Au(I)-MIC配合物:合成,结构和特性

在这里,我们报道了新型的轴向手性双-Ag(I)-MIC和带有轴向手性双-1,2,3-三唑鎓的中性离子卡宾(tz-MIC)配体的双-Au(I)-MIC配合物合成的。对映体R-BINOL被用作基本单元,以合成轴向手性双1,2,3-三唑鎓衍生的中性离子卡宾(tz-MIC)配体(1-2a。特别地,轴向手性的双-1,2,3-三唑鎓的中性离子碳烯(tz-MIC)配体(1-2a是从相应的双-1,2,3-三唑配体前体的反应获得的甲基碘和乙基碘的产率为82-90%。新型轴向手性bis-Ag(I)-MIC络合物(1-2b中,通过相应的轴向手性双- 1,2,3-三氮唑衍生的介离子卡宾(TZ-MIC)碘化物盐的处理制备,(1-2,有Ag 2澳经69 -situ去质子化方法−86%的产率。新型的轴向手性双-Au(I)-MIC配合物2c由它们各自的新型轴向手性双-Ag(I)-MIC配合物2b合成,并与(SMe 2)AuCl进行金属转移反应,产率为70%。首次分离了所有这些新颖的轴向手性双-Ag(I)-MIC和双-Au(I)-MIC配合物,并通过1 H NMR和13 C { 11 H-NMR光谱,FT-IR光谱,质谱,元素分析,比旋光度和单晶X射线晶体学。

更新日期:2020-12-04
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