1-iodo-3-(phenylethynyl)benzene | 214899-36-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 1-iodo-3-(phenylethynyl)benzene
• 英文别名: 1-Iodo-3-(2-phenylethynyl)benzene
• CAS: 214899-36-2
• 化学式: C₁₄H₉I
• 分子量: 304.13
• InChiKey: GQWDCZWZSBQXQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  1-iodo-3-(phenylethynyl)benzene 、 diphenyl(1-propynyl)phosphine oxide 在 potassium tert-butylate 、 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 22.0h， 以45%的产率得到1-(phenylethynyl)-3-(1-propynyl)benzene
  参考文献：
  名称：

  Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties

  摘要：

  A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph2N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert-Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.06.018
• 作为产物：
  描述：

  氯化苄 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.0h， 生成 1-iodo-3-(phenylethynyl)benzene
  参考文献：
  名称：

  通过加成-双消除法从芳醛一锅法合成二芳基乙炔

  摘要：

  已经开发了一种实用的一锅法，通过用 1-(芳甲基)苯并三唑和 LiN(SiMe 3 ) 2处理从芳醛合成二芳基乙炔。该反应通过亚胺形成、曼尼希型加成和双消除进行，以提供高达 99% 的产率和广泛的底物范围。此外，已经证明了 1-溴-4-(苯乙炔基)苯的克级合成。

  DOI：

  10.1039/d1ob00627d

文献信息

• Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides<i>via</i>a desulfinative process
  作者：Sheng Chang、Ying Liu、Shu Zhu Yin、Lin Lin Dong、Jian Feng Wang

  DOI：10.1039/c8nj02964d

  日期：——

  In the presence of a Pd(II)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the

  在Pd（II）/ P-配体催化体系的存在下，通过明智地选择钯催化剂或在温和条件下调节膦配体，通过脱硫偶联将炔基羧酸和芳基磺酰肼进行脱羧烷基化可以提供令人满意的收率的芳基炔烃。报道的偶联反应非常实用，因为它们不需要保护惰性气体或氧气，并且可以耐受许多官能团。
• Copper-catalyzed C(sp²)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
  作者：Wei Xu、Bo Yu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/aoc.3298

  日期：2015.6

  Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation

  通过引入催化量的多环芳烃添加剂，铜催化的Sonogashira型反应得以显着加速。这种新颖的催化系统具有低铜负载量（0.5 mol％
• Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction
  作者：Xian Wang、Zhenhua Wang、Zunyuan Xie、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c6ra23742h

  日期：——

  donor ligands were mandatory for the catalytic cross-coupling of Csp2–Csp bonds. Herein, we wish to report α,β-ynones as σ-, π-electron donating ligands for copper catalyzed Sonogashira-type reaction. As low as 0.25–2.5 mol% of L11 (3-(4-bromophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one) significantly accelerated the 0.1–1.0 mol% of CuI catalyzed cross-coupling of aryl iodides with terminal alkynes and

  在经典的反应条件下，大量的铜催化剂和N，O供体配体对于Csp 2 -Csp键的催化交叉偶联是必需的。在此，我们希望报道α，β-炔酮作为铜催化的Sonogashira型反应的σ-，π-电子给体。低至0.25–2.5 mol％的L 11（3-（4-溴苯基）-1-（4-甲氧基苯基）prop-2-yn-1-one）显着加速了0.1–1.0 mol％的CuI催化的交叉芳基碘化物分别与末端炔烃和炔基羧酸偶联。这种低摩尔％的催化剂体系具有36个取代炔烃实例，显示出令人满意的活性和耐受性。
• External oxidant-free cross-coupling of arylcopper and alkynylcopper reagents leading to arylalkyne
  作者：Sheng Wang、Yaosen Min、Xiaowei Zhang、Chanjuan Xi

  DOI：10.1039/c7ra03348f

  日期：——

  External oxidant-free oxidative cross-coupling between arylcopper and alkynylcopper has been performed, which provides a new way for the formation of arylalkyne with high selectivity.

  芳基铜和炔基铜之间进行了无外部氧化剂的氧化交叉偶联，为形成高选择性芳基炔提供了新的途径。
• Visible light-mediated gold-catalysed carbon(sp²)–carbon(sp) cross-coupling
  作者：Suhong Kim、Jaime Rojas-Martin、F. Dean Toste

  DOI：10.1039/c5sc03025k

  日期：——

  A new method for the alkynylation of aryldiazonium salts with TMS-alkynes via dual gold and photoredox catalysis is described.

  描述了一种使用双金和光氧化还原催化剂对苯基重氮盐进行炔基化反应的新方法。