tris(4-isobutoxyphenyl)bismuthane | 1239896-53-7

• 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-isobutoxyphenyl)bismuthane
• CAS: 1239896-53-7
• 化学式: C₃₀H₃₉BiO₃
• 分子量: 656.618
• InChiKey: HOIBYRFUJYMUEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-氯-3-甲酰基香豆素 、 tris(4-isobutoxyphenyl)bismuthane 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到4-(4-isobutoxyphenyl)-2-oxo-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Pd催化交叉偶联合成4-芳基-3-甲酰基香豆素

  摘要：

  三芳基铋试剂与 4-氯-3-甲酰基香豆素的三重交叉偶联以化学选择性方式在 Pd 催化条件下以高产率提供了相应的 4-芳基-3-甲酰基香豆素。该方法成功地应用于电子不同的三芳基铋试剂和保留香豆素支架中3-甲酰基的4-氯-3-甲酰基香豆素。

  DOI：

  10.1039/d1ob02016a

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。
• 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。
• 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 Synthesis of 4-Arylcoumarins Using Triarylbismuth Compounds as Atom-Efficient Multicoupling Organometallic Nucleophiles
  作者：Maddali L. N. Rao、Varadhachari Venkatesh、Deepak N. Jadhav

  DOI：10.1002/ejoc.201000134

  日期：——

  Triarylbismuth compounds have been cross-coupled as atom-efficient multicoupling organometallic nucleophiles with 4-bromo- and 4-(trifluoromethylsulfonyloxy)coumarins under palladium catalysis conditions. These reactions afforded an array of 4-arylcoumarins in high yields. The general palladium protocol has been demonstrated to be efficient for the coupling of both bromide and triflate derivatives

  在钯催化条件下，三芳基铋化合物作为原子高效多偶联有机金属亲核试剂与 4-溴和 4-（三氟甲基磺酰氧基）香豆素交叉偶联。这些反应以高产率提供了一系列 4-芳基香豆素。通用钯方案已被证明对于香豆素的溴化物和三氟甲磺酸酯衍生物与三芳基铋试剂的偶联是有效的。
• Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis
  作者：Maddali L N Rao、Jalindar B Talode、Venneti N Murty

  DOI：10.3762/bjoc.12.195

  日期：——

  A regio- and chemoselective cross-coupling study using 2,3-dibromobenzofurans and 2,3,5-tribromobenzofuran was achieved with sub-stoichiometric loadings of triarylbismuths as atom-economic reagents under Pd-catalyzed conditions. As part of this study, various 2,3-diaryl- and 2,3,5-triarylbenzofuran products were obtained in high yields, involving one-pot operations and short reaction times.

  使用亚化学和选择性交叉偶联研究，利用2,3-二溴苯并呋喃和2,3,5-三溴苯并呋喃，采用亚化学试剂三芳基铋的亚化学负载，在Pd催化条件下实现。在这项研究的一部分中，通过一锅操作和短反应时间，得到了各种2,3-二芳基和2,3,5-三芳基苯并呋喃产品，收率高。