Tris(4-prop-2-enoxyphenyl)bismuthane | 1248383-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Tris(4-prop-2-enoxyphenyl)bismuthane
• CAS: 1248383-98-3
• 化学式: C₂₇H₂₇BiO₃
• 分子量: 608.49
• InChiKey: CVOFMLPLDHYNDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tris(4-prop-2-enoxyphenyl)bismuthane 、 1-[4-(氯甲基)苯基]乙酮 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以67%的产率得到1-(4-(4-(allyloxy)benzyl)phenyl)ethanone
  参考文献：
  名称：

  Threefold and chemoselective couplings of triarylbismuths with benzylic chlorides and iodides using palladium catalysis

  摘要：

  本文描述了对三芳基铋试剂与苄基氯和碘进行三重偶联的钯催化研究。经过优化的实验条件操作简单，使得多种三芳基铋与苄基氯和碘的三重偶联得以实现。这两种优化的实验方案使得不对称二芳基甲烷的合成变得高效。在本研究的过程中，还实现了苄基氯和碘的化学选择性转化。

  DOI：

  10.1039/c3ra46672h

文献信息

• Pd-Catalyzed Threefold Arylation of Baylis-Hillman Bromides and Acetates with Triarylbismuth Reagents
  作者：Maddali L. N. Rao、Somnath Giri

  DOI：10.1002/ejoc.201200543

  日期：2012.8

  alkyl 2-benzylacrylates and 2-benzylacrylonitriles were synthesized by means of atom-economic cross-couplings of Baylis–Hillman bromides or acetates with BiAr3 under palladium-catalyzed conditions. These reactions, involving threefold aryl couplings using BiAr3 reagents with bromides and acetates, are fast and are completed in 1–2 h with high product yields.

  在钯催化条件下，通过 Baylis-Hillman 溴化物或乙酸盐与 BiAr3 的原子经济交叉偶联合成了功能化的 2-苄基丙烯酸烷基酯和 2-苄基丙烯腈。这些反应涉及使用 BiAr3 试剂与溴化物和乙酸盐进行三重芳基偶联，反应速度快，在 1-2 小时内完成，产品收率高。
• Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1002/ejoc.201402455

  日期：2014.8

  Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot

  公开了在 Pd 催化条件下使用溴吡啶和溴喹啉与三芳基铋作为亚化学计量量的三重偶联试剂的交叉偶联研究。与单-和二溴吡啶基底物的反应性很高，并且单-和双-偶联是区域选择性地进行的。以高产率形成了单芳基和二芳基吡啶库。一锅法提供了对称和不对称二芳基吡啶的简单直接合成。使用三芳基铋试剂实现了 2-溴和 3-溴喹啉的芳基化。该研究表明，三芳基铋可用作三重芳基化试剂，用于在 Pd 催化条件下通过与溴吡啶和溴喹啉偶联合成芳基吡啶和喹啉。
• Oxalyl chloride as carbonyl synthon in Pd-catalyzed carbonylations of triarylbismuth and triarylindium organometallic nucleophiles
  作者：Maddali L.N. Rao、Varadhachari Venkatesh、Priyabrata Dasgupta

  DOI：10.1016/j.tetlet.2010.07.074

  日期：2010.9

  demonstrated to function as C1 carbonyl synthon in the carbonylations of triarylbismuth and triarylindium nucleophiles under palladium-catalyzed conditions. All the three aryl groups from both bismuth and indium reagents participated in carbonylative couplings to afford the corresponding functionalized ketones in high yields. This study also disclosed a novel utilization of oxalyl chloride as facile

  已证明草酰氯在钯催化条件下在三芳基铋和三芳基lin亲核试剂的羰基化反应中充当C1羰基合成子。来自铋和铟试剂的所有三个芳基均参与羰基化偶联，以高收率提供相应的官能化酮。这项研究还公开了草酰氯作为钯催化下羰基化反应的便捷的CO替代来源的新用途。
• Palladium catalyzed atom-economic synthesis of functionalized 9-(diarylmethylene)-9H-fluorenes using triarylbismuths in one-pot bis-coupling process
  作者：Maddali L.N. Rao、Priyabrata Dasgupta

  DOI：10.1016/j.tetlet.2011.10.156

  日期：2012.1

  An efficient palladium catalyzed atom-economic synthesis of functionalized 9-(diarylmethylene)-9H-fluorenes has been accomplished in one-pot bis-coupling process using triarylbismuths as organometallic reagents. These bis-couplings in 1 hour short reaction time afforded various 9-(diarylmethylene)-9H-fluorenes in good to high yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Threefold and chemoselective couplings of triarylbismuths with benzylic chlorides and iodides using palladium catalysis
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1039/c3ra46672h

  日期：——

  This paper describes the palladium-catalyzed studies on threefold coupling of triarylbismuth reagents with benzylic chlorides and iodides. The optimized protocol conditions are operationally simple, delivering threefold coupling of a variety of triarylbismuths in combination with benzylic chlorides and iodides. The two optimized protocols allowed the synthesis of a diverse range of unsymmetrical diarylmethanes in an efficient manner. As part of this study, chemoselective transformation of benzylic chlorides and iodides was also achieved.

  本文描述了对三芳基铋试剂与苄基氯和碘进行三重偶联的钯催化研究。经过优化的实验条件操作简单，使得多种三芳基铋与苄基氯和碘的三重偶联得以实现。这两种优化的实验方案使得不对称二芳基甲烷的合成变得高效。在本研究的过程中，还实现了苄基氯和碘的化学选择性转化。