([1,1′-biphenyl]-2-yloxy)diisopropylphosphine | 433336-98-2

• 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: ([1,1′-biphenyl]-2-yloxy)diisopropylphosphine
• 英文别名: ([1,1'-biphenyl]-2-yloxy)diisopropylphosphine；2-phenylphenyl diisopropylphosphinite；2-phenylphenol diisopropylphosphinite；P(i)Pr2(OC6H4-2-Ph)；(2-Phenylphenoxy)-di(propan-2-yl)phosphane
• CAS: 433336-98-2
• 化学式: C₁₈H₂₃OP
• 分子量: 286.354
• InChiKey: FTTQOEVSAMXQEC-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ([1,1′-biphenyl]-2-yloxy)diisopropylphosphine 在 dimethyl sulfide borane 、 双三氟甲烷磺酰亚胺 作用下， 以 甲醇 、 氟苯 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 (2-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾
  参考文献：
  名称：

  P-Directed Borylation of Phenols

  摘要：

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

  DOI：

  10.1021/ol303203m
• 作为产物：
  描述：

  邻苯基苯酚 在 三乙胺 、 氯二异丙基膦 作用下， 以 甲苯 为溶剂， 反应 16.25h， 以92%的产率得到([1,1′-biphenyl]-2-yloxy)diisopropylphosphine
  参考文献：
  名称：

  使用Bedford型palladacycle催化剂将乙酸肉桂酯与四苯硼酸钠进行烯丙基芳基化的水溶液方案†

  摘要：

  描述了使用0.002mol％的贝德福德型Palladacycle催化剂，使乙酸肉桂酯与四苯基硼酸钠进行烯丙基芳基化。所开发的方法学适用于各种乙酸肉桂酯，可提供高达93％的极佳收率。值得注意的是，所有反应在空气气氛下在温和的反应条件下在水中顺利进行。

  DOI：

  10.1039/c8nj00660a

文献信息

• Facile palladium catalyzed Suzuki–Miyaura coupling in air and water at ambient temperature
  作者：Alexander N. Marziale、Stefan H. Faul、Thomas Reiner、Sven Schneider、Jörg Eppinger

  DOI：10.1039/b915436a

  日期：——

  A new palladacyclic catalyst yields high activities in aqueous Suzuki–Miyaura coupling at room temperature. Using an optimized protocol, a broad range of products can be isolated in good to excellent yields and high purity by simple filtration.

  在室温下，新型的五环催化剂在铃木-宫浦水溶液偶联中具有很高的活性。使用优化的方案，可以通过简单的方法分离出范围广泛的产品，并具有良好的收率，高纯度和高纯度过滤。
• Orthopalladated phosphinite complexes as high-activity catalysts for the Suzuki reaction
  作者：Robin B. Bedford、Samantha L. Hazelwood (née Welch)、Peter N. Horton、Michael B. Hursthouse

  DOI：10.1039/b303657j

  日期：——

  phosphinite ligands PR2(OAr) (R = Ph, iPr), their simple complexes with palladium(II) and their palladacyclic complexes has been investigated. The crystal structure of one of the palladacyclic complexes, [Pd(μ2-Cl)κ2-P,C-PiPr2(OC6H2-2,4-tBu2)}2], has been determined. The palladacyclic complexes show extremely high activity in the Suzuki coupling of aryl bromide substrates with phenylboronic acid and can

  一系列次膦酸酯的合成 配体PR 2（OAr）（R = Ph，i Pr），它们与钯（II）的简单配合物及其钯环配合物已得到研究。所述palladacyclic络合物中的一个的晶体结构，[的Pd（μ 2 -Cl）κ 2 - P，Ç -P我镨2（OC 6 H ^ 2 -2,4-吨卜2）} 2 ]，有被确定。Palladacyclic配合物在芳基溴化物底物与Suzuki偶联的Suzuki偶联中显示出极高的活性苯硼酸还可与烷基硼酸底物一起使用。次膦酸酯基的比较催化剂与基于亚磷酸酯和膦的体系相当的产品突显了其卓越的活性。次膦酸酯的原金属化配体在预催化剂中似乎对于最佳活性至关重要。尽管次膦酸酯四环化合物仅在活化和未活化的芳基氯化物底物的偶联中具有中等活性，但它们的三环己基膦 加合物在失活的底物偶联中被证明具有很高的活性， 4-氯茴香醚。与其他四环系统相比，这种高活性的解释是：催化剂长寿。原金属化的预
• An efficient protocol for copper-free palladium-catalyzed Sonogashira cross-coupling in aqueous media at low temperatures
  作者：Alexander N. Marziale、Johannes Schlüter、Jörg Eppinger

  DOI：10.1016/j.tetlet.2011.09.031

  日期：2011.11

  A thorough study on copper-free Sonogashira cross-couplings in water was carried out using the palladacycle, [Pd(μ-Cl)κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2] as pre-catalyst with different bases and palladium concentrations. The highly active pre-catalyst imparts good to near quantitative yields using a concentration of 0.25 mol % at 40 °C. This broadly applicable protocol exhibits high tolerance of functional

  在水中无铜的Sonogashira交叉偶联彻底进行了研究，使用的钯，[的Pd（μ-Cl）的κ 2 -P，CP（我PR）2（OC 6 H ^ 3 -2-PH） }} 2 ]作为具有不同碱和钯浓度的预催化剂。在40°C下使用0.25 mol％的浓度，高活性预催化剂可提供良好的定量收率。这种广泛适用的协议展现出对功能基团和​​取代模式的高度耐受性。
• Bedford-Type Palladacycle-Catalyzed Miyaura Borylation of Aryl Halides with Tetrahydroxydiboron in Water
  作者：Anna Zernickel、Weiyuan Du、Seema A. Ghorpade、Dinesh N. Sawant、Arwa A. Makki、Nagaiyan Sekar、Jörg Eppinger

  DOI：10.1021/acs.joc.7b02771

  日期：2018.2.16

  A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 degrees C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
• Aqueous protocol for allylic arylation of cinnamyl acetates with sodium tetraphenylborate using a Bedford-type palladacycle catalyst
  作者：Seema Arun Ghorpade、Dinesh Nanaji Sawant、Dominik Renn、Anna Zernickel、Weiyuan Du、Nagaiyan Sekar、Jörg Eppinger

  DOI：10.1039/c8nj00660a

  日期：——

  Allylic arylation of cinnamyl acetates with sodium tetraphenylborate using 0.002 mol% of a Bedford-type palladacycle catalyst is described. The developed methodology is applicable for a wide range of cinnamyl acetates furnishing excellent yields of up to 93%. Notably all reactions proceed smoothly under mild reaction conditions in water under an air atmosphere.

  描述了使用0.002mol％的贝德福德型Palladacycle催化剂，使乙酸肉桂酯与四苯基硼酸钠进行烯丙基芳基化。所开发的方法学适用于各种乙酸肉桂酯，可提供高达93％的极佳收率。值得注意的是，所有反应在空气气氛下在温和的反应条件下在水中顺利进行。