tris(3,4-dimethoxyphenyl)bismuthane | 895154-77-5

• 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: tris(3,4-dimethoxyphenyl)bismuthane
• CAS: 895154-77-5
• 化学式: C₂₄H₂₇BiO₆
• 分子量: 620.455
• InChiKey: RKKFNVUIYWINOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氯吡啶 、 tris(3,4-dimethoxyphenyl)bismuthane 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以92%的产率得到2-(3,4-二甲氧基苯基)吡啶
  参考文献：
  名称：

  Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

  摘要：

  This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines in high yields. The couplings addressed with dihalopyridines have afforded chemo- and regio-selective coupling products. Arylations of 2-chloroquinoline with different triarylbismuth reagents demonstrated fruitful coupling reactivity under the established conditions. This sumptuous study demonstrates the remarkable cross-coupling reactivity of iodo/chloropyridines and chloroquinoline with triarylbismuth reagents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.036
• 作为产物：
  描述：

  邻苯二甲醚 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 20.5h， 生成 tris(3,4-dimethoxyphenyl)bismuthane
  参考文献：
  名称：

  通过简洁的合成策略快速获取基于苯并呋喃的天然产品

  摘要：

  描述了用于合成臭椿素 (1)、egonol (2)、homoegonol (3)、demethoxyegonol (4)、demethoxyhomoegonol (5) 和 Stemofuran A (6) 的简明策略。该方法涉及使用三芳基铋试剂生成苯并呋喃核的 Pd 催化的多米诺环化/偶联过程。随后的结构修改然后给出最终目标。最近分离的天然产物 egonol-9(Z)-12(Z)-linoleate (2a)、7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 和 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 的高产合成-egonol-9(Z)-油酸酯 (4b) 也有报道。

  DOI：

  10.1002/ejoc.201600154

文献信息

• Pot-economic synthesis of diarylpyrazoles and pyrimidines involving Pd-catalyzed cross-coupling of 3-trifloxychromone and triarylbismuth
  作者：Abhijeet Kumar、Maddali L N Rao

  DOI：10.1007/s12039-018-1565-6

  日期：2018.12

  of isoflavone via cross-coupling reaction of 3-trifloxychromone and triarylbismuth as a threefold arylating reagent. These isoflavones were further converted into 3,4-diarylpyrazole and 4,5-diarylpyrimidine using hydrazine hydrate and guanidinium chloride in the successive step in the same pot. Interestingly the formation of 3,4-diarylpyrazole was achieved in the shortest reaction time i.e., 30 min

  摘要本研究揭示了从3-trifloxychromone和triarylbismuth开始的一锅操作中3,4-二芳基吡唑和4,5-二芳基嘧啶的形成。一站式操作中，整个过程包括两个步骤。第一步通过作为三重芳基化试剂的3-三氟甲氧基色酮和三芳基铋的交叉偶联反应导致异黄酮的形成。在同一罐中的后续步骤中，使用水合肼和氯化胍将这些异黄酮进一步转化为3,4-二芳基吡唑和4,5-二芳基嘧啶。有趣的是，在最短的反应时间即在室温下也达到了30分钟，就形成了3,4-二芳基吡唑。 图形概要 提要此处介绍的工作描述了一种新的方法，该方法可通过一锅操作从3-三氟甲氧色酮和三芳基铋开始形成具有医学重要性的杂环3,4-二芳基吡唑和4,5-二芳基嘧啶。
• 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。
• Atom-economic threefold cross-couplings of triarylbismuth reagents with 2-halobenzaldehydes and pot-economic in situ Wittig functionalizations with phosphonium salts
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1039/c4ra13348j

  日期：——

  In this paper we report an efficient pot-economic methodology for the synthesis of ortho-olefinated biaryls. This has been achieved through an atom-economic threefold cross-coupling of triarylbismuth reagents with 2-halobenzaldehydes followed by pot-economic in situ Wittig olefination. The overall process is a pot-economic straightforward synthesis of ortho-olefinated biaryls from 2-halobenzaldehydes, triarylbismuth reagents and phosphonium salts. This pot-economic approach was applied to the formal synthesis of medicinally important Eupomatilone-6.

  本文报道了一种高效的原位Wittig烯化反应方法，用于合成邻烯基联苯。通过三芳基铋试剂与2-卤代苯甲醛的三重交叉偶联，继而进行原位Wittig烯化，实现了这一目标。整个过程是从2-卤代苯甲醛、三芳基铋试剂和膦盐出发，高效简便地合成邻烯基联苯。这一方法已成功应用于重要的药用成分Eupomatilone-6的正式合成中。
• Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2014.07.059

  日期：2014.9

  4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2–4 h conditions

  在钯催化下，使用三芳基铋作为三重芳基化试剂，研究了不同取代的4-氯香豆素的交叉偶联反应。证明了4-氯香豆素的高反应性以化学选择性方式递送单芳基化和双芳基化产物。所采用的反应条件简单，稳定，并且在2-4小时的条件下，三芳基铋试剂的三重偶联反应性得到了良好的证明。在合成一些天然存在的新黄酮（3.27 – 3.30）中探索了该方法的实用性。另外，4-芳基香豆素3.1产物是制备（R）-托特罗定的有用前体。
• 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。