(1-(4-fluorophenyl)ethane-1,2-diyl)bis(diphenylphosphine) | 1387578-78-0

• 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-(4-fluorophenyl)ethane-1,2-diyl)bis(diphenylphosphine)
• 英文别名: 1,2-bis(diphenylphosphino)-1-(4-fluorophenyl)ethane；[2-Diphenylphosphanyl-1-(4-fluorophenyl)ethyl]-diphenylphosphane
• CAS: 1387578-78-0
• 化学式: C₃₂H₂₇FP₂
• 分子量: 492.512
• InChiKey: WUOKDIBXWJONBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氟苯乙炔 、 二苯基膦 在 cyclopentadienyl iron(II) dicarbonyl dimer 作用下， 以 neat (no solvent) 为溶剂， 反应 4.0h， 以99%的产率得到(1-(4-fluorophenyl)ethane-1,2-diyl)bis(diphenylphosphine)
  参考文献：
  名称：

  使用市售铁化合物对末端炔烃进行可见光和热驱动的双氢磷酸化反应

  摘要：

  市售的铁化合物，[CpFe的量（CO）2 ] 2（1）（CP =η 5 -C 5 H ^ 5），是用于与二苯基膦可见光照射或热的条件下末端芳炔烃组成的双hydrophosphination一个有效的催化剂与文献报道相比，某些底物的反应时间缩短了两个数量级。在这些反应中产生的1,2-双（二苯基膦基）乙烷产物很容易以高收率分离。

  DOI：

  10.1039/c8cc00847g

文献信息

• Regioselective Double Hydrophosphination of Terminal Arylacetylenes Catalyzed by an Iron Complex
  作者：Masahiro Kamitani、Masumi Itazaki、Chihiro Tamiya、Hiroshi Nakazawa

  DOI：10.1021/ja304818c

  日期：2012.7.25

  The first catalytic double hydrophosphination of alkynes was achieved by reaction with diarylphosphines in the presence of an iron catalyst. The double hydrophosphination proceeded regioselectively and effectively for various secondary arylphosphines and terminal alkynes to give 1,2-bisphosphinoethane derivatives.

  炔烃的第一次催化双氢膦化反应是通过在铁催化剂存在下与二芳基膦反应实现的。双氢膦化反应对各种仲芳基膦和末端炔烃进行区域选择性和有效的反应，得到 1,2-双膦基乙烷衍生物。
• Sequential Addition of Phosphine to Alkynes for the Selective Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined NHC-Copper Phosphides vs in Situ CuCl₂/NHC Catalyst
  作者：Jia Yuan、Lizhao Zhu、Jianying Zhang、Jianfeng Li、Chunming Cui

  DOI：10.1021/acs.organomet.6b00854

  日期：2017.1.23

  The well-defined NHC-copper phosphides [(NHC)CuPPh2](3) (1, NHC = 1,3-diisopropy1-4,5-dimethyli- midazol-2-ylidene (I'Pr); 2, NHC = N,N-di-tert-butylimidazol-2-ylidene ((IBu)-Bu-t)) have been prepared by the reaction of simple copper halides with HPPh2 in the presence of N-heterocyclic carbenes (NHCs). Complexes 1 and 2 enabled catalytic double hydrophosphination of alkyl and aryl terminal alkynes to yield 1,2-diphosphinoethanes selectively in good yields. On the basis of these results, the most efficient and pratical in situ CuCl2/NHC catalyst has been developed. It catalyzes the selective double hydrophosphination of the alkynes with high efficiency and a wide substrate scope and exhibits even better performance than the well-defined NHC-Cu phosphides. The mechanistic studies disclosed that the formation of a copper acetylide in the catalytic cycle played an important role in the acceleration of the catalytic process.