tri([1,1′-biphenyl]-4-yl)bismuth | 29712-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tri([1,1′-biphenyl]-4-yl)bismuth
• 英文别名: tri([1,1'-biphenyl]-4-yl)bismuthane；Bi(C6H4-p-C6H5)3；tris-biphenyl-4-yl-bismuthine；Tris-(biphenylyl-(4))-wismut；Tris-biphenyl-4-yl-bismutin
• CAS: 29712-10-5
• 化学式: C₃₆H₂₇Bi
• 分子量: 668.591
• InChiKey: LPNVCKCRJQQPEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tri([1,1′-biphenyl]-4-yl)bismuth 在 氯 作用下， 以 四氯化碳 为溶剂， 以>99的产率得到(p-C6H5C6H4)3BiCl2
  参考文献：
  名称：

  Some Bismuth Derivatives of Diphenyl

  摘要：

  DOI：

  10.1021/ja01300a507
• 作为产物：
  描述：

  2-BIPHENYLMAGNESIUM BROMIDE 、 氯化铋 以 乙醚 为溶剂， 以50%的产率得到tri([1,1′-biphenyl]-4-yl)bismuth
  参考文献：
  名称：

  Some Bismuth Derivatives of Diphenyl

  摘要：

  DOI：

  10.1021/ja01300a507

文献信息

• Rapid Bis-Coupling Reactivity with Triarylbismuth Reagents: Synthesis of Structurally Diverse Scaffolds and Step-economic Convergent Synthesis of Quebecol
  作者：Maddali L. N. Rao、Venneti N. Murty、Sachchida Nand

  DOI：10.1002/ejoc.201901830

  日期：2020.3.22

  The cross‐coupling study of gem‐dibromoesters with triarylbismuths furnished a variety of multi‐functional trisubstituted acrylates embedded with aryl, alkene and alkyne scaffolds in high yields under palladium catalysis. Further, the established method was applied in the step‐economic and convergent synthesis of quebecol natural product in good yield.

  宝石二溴酸酯与三芳基铋的交叉偶联研究提供了在钯催化下高产率嵌入芳基，烯烃和炔烃骨架的多种多功能三取代丙烯酸酯。此外，已建立的方法被用于步伐经济和收敛合成高品质的魁北克天然产物。
• Sulfonylation of Bismuth Reagents with Sulfinates or SO₂ through Bi^III/Bi^V Intermediates
  作者：Fengqian Zhao、Xiao-Feng Wu

  DOI：10.1021/acs.organomet.1c00339

  日期：2021.8.9

  Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)–Bi(V)

  探索主族元素催化活性的研究很有吸引力。我们在此报告我们对铋试剂与亚磺酸盐或 SO 2替代物磺酰化的研究。在氧化条件下，三芳基铋和亚磺酸盐转化为二芳基砜。该反应在Bi中心实现了类似过渡金属的双电子氧化还原过程。原位生成的二氧化硫也可以替代亚磺酸盐以提供相应的对称二芳基砜。还提出了该反应的合理机制，涉及 Bi(III)-Bi(V) 流形。
• Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds
  作者：Tao Wang、Shuai Sang、Liu Leo Liu、Hongwei Qiao、Yuxing Gao、Yufen Zhao

  DOI：10.1021/jo402392t

  日期：2014.1.17

  A novel and highly efficient Pd-catalyzed cross-coupling of triarylbismuths with a variety of P(O)–H compounds has been developed that proceeds smoothly without exclusion of moisture or air and provides a general and powerful tool for the preparation of various valuable arylphosphonates, arylphosphinates, and arylphosphine oxides, with high atom-economy, operational simplicity of the procedure, and

  已开发出新颖且高效的Pd催化的三芳基铋与各种P（O）–H化合物的交叉偶合，该过程平稳进行且不排除水分或空气，为制备各种有价值的芳基膦酸酯提供了通用而强大的工具，芳基次膦酸酯和芳基膦氧化物，具有高原子经济性，该方法的操作简单，并且良好至高收率。偶联反应是使用三芳基铋化合物作为底物的过渡金属催化的C-P键结构的第一个例子。DFT计算表明，C-P键的形成是决定速率的步骤。
• High efficient copper-promoted N-arylation of secondary and primary amines with triarylbismuth reagents under mild conditions
  作者：Xuehao Zhou、Huifang Ma、Jianwei Xie

  DOI：10.1016/j.molstruc.2023.136437

  日期：2023.12

  Triarylbismuths were found to be highly efficient arylating reagents for copper-promoted N-arylation of secondary and some heteroaryl and aliphatic primary amines with over 49 examples. A variety of sterically diverse tertiary and secondary amines could be obtained in good to excellent yields with good functional group compatibility. The operational simplicity, mild reaction conditions as well as the

  三芳基铋被发现是高效的芳基化试剂，可用于铜促进的仲胺、一些杂芳基和脂肪族伯胺的 N-芳基化，有超过 49 个实例。可以以良好至优异的产率获得各种空间不同的叔胺和仲胺，并且具有良好的官能团相容性。操作简单、反应条件温和以及有效的克级制备选项使该工艺更加实用。
• Copper-promoted <i>S</i>-arylation reactions with triarylbismuths for the synthesis of diaryl sulfides
  作者：Mei Nie、Xuehao Zhou、Jingjie Tang、Dongting Huang、Xinsheng Xiao、Jianwei Xie

  DOI：10.1039/d3ra06582k

  日期：——

  A simple approach for copper-promoted S-arylation reactions utilizing triarylbismuths or triarylantimonys as arylating reagents has been described. These reactions can be performed under mild conditions and exhibit remarkable functional group tolerance and chemoselectivity. The corresponding 2-arylthiopyridine 1-oxide derivatives and arylthioanilines/phenols have been successfully synthesized, achieving

  已经描述了利用三芳基铋或三芳基锑作为芳基化试剂的铜促进的S-芳基化反应的简单方法。这些反应可以在温和的条件下进行，并表现出显着的官能团耐受性和化学选择性。相应的 2-芳硫基吡啶 1-氧化物衍生物和芳硫基苯胺/苯酚已成功合成，在超过 49 个实例中实现了良好至优异的产率。