2-diphenylphosphinyl-3'-nitrobiphenyl | 402822-64-4

• 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: 2-diphenylphosphinyl-3'-nitrobiphenyl
• 英文别名: 1-Diphenylphosphoryl-2-(3-nitrophenyl)benzene
• CAS: 402822-64-4
• 化学式: C₂₄H₁₈NO₃P
• 分子量: 399.386
• InChiKey: MLFAHVXDUKUXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-diphenylphosphinyl-3'-nitrobiphenyl 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of biphenyl-based phosphines by Suzuki coupling

  摘要：

  A series of phosphine oxides has been synthesised by the palladium-catalysed Suzuki coupling of arylboronic acids with OPPh2(o-C6H4Br). Oil reduction with trichlorosilane. functionalised. biphenyl-based phosphine ligands were obtained in good yields. Our preliminary results indicate these ligands to be effective for palladium-catalysed C-C coupling reactions including the formation of their own oxides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01981-5
• 作为产物：
  描述：

  邻碘溴苯 在 palladium diacetate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ potassium phosphate 、 双氧水 、 sodium acetate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 85.0h， 生成 2-diphenylphosphinyl-3'-nitrobiphenyl
  参考文献：
  名称：

  Palladium-catalysed synthesis of biaryl phosphines

  摘要：

  Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl P<^>X (X=N, O, S) phosphines with diverse steric and electronic properties. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.058

文献信息

• Palladium-catalyzed R2(O)P-directed C(sp2)-H activation
  作者：Hongyu Zhang、Shangdong Yang

  DOI：10.1007/s11426-015-5382-1

  日期：2015.8

  In recent years, transition-metal-catalyzed inert C-H bond activation has developed rapidly and is a powerful protocol for the construction of new C-C or C-X bonds and the introduction of new functional groups. Our group has also developed a series of R2(O)P-directed Pd-catalyzed C-H functionalizations involving olefination, hydroxylation, acetoxylation, arylation, and acylation through an uncommon seven-membered cyclo-palladium pretransition state. Unlike previously used directing groups, the R2(O)P group acts as a directing group and is also involved in the construction of P,-hetero-ligands.

  近年来，过渡金属催化的惰性C-H键活化发展迅速，是构建新的C-C或C-X键和引入新官能团的有力途径。我们课题组也发展了一系列R2(O)P导向的Pd催化C-H官能化反应，包括烯化、羟基化、醋酸化、芳基化和酰基化，通过一个罕见的七元环钯前过渡态。与先前使用的导向基团不同，R2(O)P基团既作为导向基团又参与构建P,-杂配体。
• Pd(II)-Catalyzed Ph₂(O)P-Directed C–H Olefination toward Phosphine–Alkene Ligands
  作者：Hong-Li Wang、Rong-Bin Hu、Heng Zhang、An-Xi Zhou、Shang-Dong Yang

  DOI：10.1021/ol402577p

  日期：2013.10.18

  The Pd(II)-catalyzed Ph-2(O)P-directed C-H olefination to synthesize alkene-phosphine compounds is reported. In contrast to previous examples of various directing groups that guide selective C-H activation, the Ph-2(O)P group not only acts as the directing group but also serves to construct the alkene-phosphine ligands. The monoprotected amino acid (MPAA) ligand Ac-Leu-OH is found to promote this reaction in a significant manner.