Bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane | 1570098-46-2

• 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: Bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane
• 英文别名: bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane
• CAS: 1570098-46-2
• 化学式: C₅₃H₇₃O₂P
• 分子量: 773.135
• InChiKey: GZMXWUIJBWCZRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane 以 二氯甲烷 、 正戊烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

  摘要：

  A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl trifiates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.

  DOI：

  10.1021/jacs.5b09308
• 作为产物：
  描述：

  4-正丁基苯硼酸 在 potassium phosphate 、 正丁基锂 、 (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1'-biphenyl)[2-(2-amino-1,1’-biphenyl)]palladium(II)methanesulfonate 、 溴 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 66.76h， 生成 Bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane
  参考文献：
  名称：

  Pd-Catalyzed Nucleophilic Fluorination of Aryl Bromides

  摘要：

  On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.

  DOI：

  10.1021/ja5009739
• 作为试剂：
  描述：

  1,1-diphenylprop-1-en-2-yl trifluoromethanesulfonate 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 Bis(1-adamantyl)-[2-[3-(4-butylphenyl)-2,4,6-tri(propan-2-yl)phenyl]-3,6-dimethoxyphenyl]phosphane 、 cesium fluoride 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到(2-氟-1-苯基丙-1-烯基)苯
  参考文献：
  名称：

  钯催化的环乙烯基三氟甲磺酸酯氟化：TESCF3作为添加剂的作用

  摘要：

  已经开发了钯催化的环状乙烯基三氟甲磺酸酯氟化方法。与以前使用氟化物盐进行的钯催化的氟化反应一样，控制区域选择性对开发实用的合成方法提出了挑战。加入三乙基（三氟甲基）硅烷（TESCF 3）被发现可以有效地解决这个问题，并在钯催化的氟化反应中显着提高了区域选择性。这一发现，加上使用新的联芳基膦配体，为氟代三氟甲磺酸酯的氟化开发了一种高效且高度区域选择性的方案。该方法与一系列敏感的官能团兼容，并可以使用五元，六元和七元环状氟乙烯。

  DOI：

  10.1002/anie.201608927

文献信息

• A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
  作者：Aaron C. Sather、Hong Geun Lee、Valentina Y. De La Rosa、Yang Yang、Peter Müller、Stephen L. Buchwald

  DOI：10.1021/jacs.5b09308

  日期：2015.10.21

  A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl trifiates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.
• Pd-Catalyzed Nucleophilic Fluorination of Aryl Bromides
  作者：Hong Geun Lee、Phillip J. Milner、Stephen L. Buchwald

  DOI：10.1021/ja5009739

  日期：2014.3.12

  On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.