tris(4-acetylphenyl)bismuth | 1174747-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tris(4-acetylphenyl)bismuth
• CAS: 1174747-46-6
• 化学式: C₂₄H₂₁BiO₃
• 分子量: 566.409
• InChiKey: LBQRAPJZENYBOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tris(4-acetylphenyl)bismuth 、 3-氯-6-碘哒嗪 在 palladium diacetate 、 三苯基膦 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以55%的产率得到3-chloro-6-(4-acetylphenyl)pyridazine
  参考文献：
  名称：

  三芳基或三杂芳基铋化合物与 3,6-二卤代哒嗪的 Pd 催化化学选择性交叉偶联反应

  摘要：

  3,6-二卤代哒嗪与三芳基-或三杂芳基铋化合物的交叉偶联反应在钯催化下进行。该反应具有高度化学选择性，以中等至良好的产率提供官能化的芳基-或杂芳基哒嗪基氯。

  DOI：

  10.1002/ejoc.201200977

文献信息

• Pd(0)/C-catalyzed cross-couplings of acyl chlorides with triarylbismuths as atom-efficient sub-stoichiometric multi-coupling reagents
  作者：Maddali L.N. Rao、Deepak N. Jadhav、Varadhachari Venkatesh

  DOI：10.1016/j.tetlet.2009.05.003

  日期：2009.7

  Aromatic and hetero-aromatic acyl chlorides were efficiently cross-coupled with triarylbismuths as atom-efficient nucleophilic organometallic coupling reagents in sub-stoichiometric amounts using catalytic Pd(0)/C. Thus, the coupling reactions of various triarylbismuths with a variety of acyl chlorides furnished a plethora of both symmetrical/unsymmetrical aromatic and hetero-aromatic ketones in high

  使用催化的Pd（0）/ C，亚化学计量的芳香族和杂芳香族酰氯与三芳基铋有效地交叉偶联，成为原子有效的亲核有机金属偶联剂。因此，各种三芳基铋与各种酰氯的偶联反应以高收率提供了大量对称/不对称的芳族和杂芳族酮。
• Atom-Efficient Vinylic Arylations with Triarylbismuths as Substoichiometric Multicoupling Reagents under Palladium Catalysis
  作者：Maddali L. N. Rao、Deepak N. Jadhav、Varadhachari Venkatesh

  DOI：10.1002/ejoc.200900487

  日期：2009.9

  The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  通过在钯催化下使用三芳基铋作为亚化学计量的多偶联试剂，实现了乙烯基碘的第一个原子有效芳基化。乙烯基碘化物与电子发散的三芳基铋有效偶联，以在较短的反应时间内提供相应的芳基化产物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles
  作者：Maddali L. N. Rao、Deepak N. Jadhav、Priyabrata Dasgupta

  DOI：10.1021/ol1004164

  日期：2010.5.7

  The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.
• Pd-Catalyzed Chemoselective Cross-Coupling Reaction of Triaryl- or Triheteroarylbismuth Compounds with 3,6-Dihalopyridazines
  作者：Karène Urgin、Christophe Aubé、Muriel Pipelier、Virginie Blot、Christine Thobie-Gautier、Stéphane Sengmany、Jacques Lebreton、Eric Léonel、Didier Dubreuil、Sylvie Condon

  DOI：10.1002/ejoc.201200977

  日期：2013.1

  The cross-coupling reactions of 3,6-dihalopyridazines with triaryl- or triheteroarylbismuth compounds were performed under palladium catalysis. The reaction was highly chemoselective, affording functionalized aryl- or heteroarylpyridazinyl chlorides in moderate to good yields.

  3,6-二卤代哒嗪与三芳基-或三杂芳基铋化合物的交叉偶联反应在钯催化下进行。该反应具有高度化学选择性，以中等至良好的产率提供官能化的芳基-或杂芳基哒嗪基氯。