cis-NCC6H4B(OH)2O2Pd(PPh3)2 | 889649-62-1

• 英文名称: cis-NCC6H4B(OH)2O2Pd(PPh3)2
• CAS: 889649-62-1
• 化学式: C₄₃H₃₆BNO₄P₂Pd
• 分子量: 809.942
• InChiKey: SQGHLEBXJZPHLE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  (η2-peroxo)bis(triphenylphosphine)palladium 、 4-氰基苯硼酸 以 氘代氯仿 为溶剂， 生成 cis-NCC6H4B(OH)2O2Pd(PPh3)2
  参考文献：
  名称：

  Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids:  Key Involvement of a Palladium Peroxo Complex

  摘要：

  The mechanism of the palladium-catalyzed homocoupling of arylboronic acids ArB(OH)(2) (Ar = 4-Z-C6H4 with Z = MeO, H, CN) in the presence of dioxygen, leading to symmetrical biaryls, has been fully elucidated. The peroxo complex (eta(2)-O-2)PdL2 (L = PPh3), generated in the reaction of dioxygen with the Pd(0) catalyst, was found to play a crucial role. Indeed, it reacts with the arylboronic acid to generate an adduct (coordination of one oxygen atom of the peroxo complex to the oxophilic boron atom of the arylboronic acid) characterized by P-31 NMR spectroscopy and ab initio calculations. This adduct reacts with a second molecule of arylboronic acid to generate trans-ArPd(OH)L-2 complexes. A transmetalation by the arylboronic acid gives trans-ArPdArL2 complexes. The biaryl is then released in a reductive elimination. This reaction is at the origin of the formation of biaryls as byproducts in palladium-catalyzed Suzuki-Miyaura reactions when they are not conducted under oxygen-free atmosphere.

  DOI：

  10.1021/ja0569959