(S)-(2,4-dimethyl-5-oxo-2,5-dihydrofuran-3-yl)(triphenyl-l5-phosphaneyl)gold | 1094064-53-5

• 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: (S)-(2,4-dimethyl-5-oxo-2,5-dihydrofuran-3-yl)(triphenyl-l5-phosphaneyl)gold
• CAS: 1094064-53-5
• 化学式: C₂₄H₂₂AuO₂P
• 分子量: 570.378
• InChiKey: HHJGDOQVSFMCTF-UTYJZAQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (S)-(2,4-dimethyl-5-oxo-2,5-dihydrofuran-3-yl)(triphenyl-l5-phosphaneyl)gold 、 对溴苯甲醛 在 dichlorobis(tricyclohexylphosphine)nickel(II) 作用下， 以 苯 为溶剂， 反应 4.0h， 以40%的产率得到C₁₃H₁₂O₃
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Coupling of Organogold Reagents

  摘要：

  Organogold compounds undergo nickel-catalyzed cross-coupling reactions with aryl and vinyl bromides in high yield under mild conditions. The reaction tolerates both electron-rich and electron-poor organogold complexes, and olefinic bromides undergo cross-coupling with high stereoselectivity. This novel transformation links well-established nickel catalysis with more recent developments in organogold transformations.

  DOI：

  10.1021/om200060x
• 作为产物：
  描述：

  三苯基膦氯金 、 tert-butyl 2-methylpenta-2,3-dienoate 在 2,6-di-tert-butylpyridine 、 AgOTf 作用下， 以 CH₂Cl₂ 为溶剂， 以67%的产率得到(S)-(2,4-dimethyl-5-oxo-2,5-dihydrofuran-3-yl)(triphenyl-l5-phosphaneyl)gold
  参考文献：
  名称：

  Relative Kinetic Basicities of Organogold Compounds

  摘要：

  The relative kinetic basicities of a series of differentially substituted and hybridized neutral organogold compounds were examined through competitive protodeauration experiments and were found to span 2.2 orders of magnitude. The effect of electron-withdrawing and electron-donating substituents on the rate of protodeauration of alkenylgold and arylgold compounds was explored. An acid counterion effect indicated the presence of a gold-mediated substrate preequilibrium before protodemetalation, and hybridization effects and a Hammett correlation with rho(+) = -0.41 indicated the involvement of the C-C pi system in the protodeauration of vinylgold, alkynylgold, and arylgold complexes.

  DOI：

  10.1021/om901101f

文献信息

• Synthesis and Structural Characterization of Stable Organogold(I) Compounds. Evidence for the Mechanism of Gold-Catalyzed Cyclizations
  作者：Le-Ping Liu、Bo Xu、Mark S. Mashuta、Gerald B. Hammond

  DOI：10.1021/ja806685j

  日期：2008.12.31

  nucleophile attacks a gold-activated carbon-carbon multiple bond to give an alkenyl Au intermediate, notwithstanding the fact that these intermediates are hitherto unknown. We have obtained room temperature stable gamma-lactone gold(I) complexes through the reaction of cationic Au(I) reagents with allenoates, under mild conditions. The reactions of one such complex with electrophiles yielded the expected products

  绝大多数均相 Au 催化反应利用 Au 作为亲电子试剂活化不饱和碳-碳键的倾向。通常假设亲核试剂攻击金活化的碳-碳多键以产生烯基 Au 中间体，尽管这些中间体迄今为止是未知的。我们通过阳离子 Au(I) 试剂与烯丙酸在温和条件下反应获得了室温稳定的 γ-内酯金 (I) 配合物。一种这样的配合物与亲电试剂的反应产生了金催化环化的预期产物。这些结果为 Au 催化环化的机理提供了实验证据。
• Catalytic Cross-Coupling of Vinyl Golds with Diazonium Salts under Photoredox and Thermal Conditions
  作者：Dilip V. Patil、Hokeun Yun、Senghoon Shin

  DOI：10.1002/adsc.201500525

  日期：2015.8.24

  Catalytically generated vinyl gold complexes from tert‐butyl allenoates were found to undergo an efficient cross‐coupling with arenediazonium salts. The gold(I)‐gold(III) redox cycle can be accessed under two different conditions, i.e., visible‐light photoredox as well as a thermally induced radical chain pathway. The current C(sp2)C(sp2) cross‐coupling protocol that is catalytic in gold, would make available

  发现由烯丙基叔丁基酯催化生成的乙烯基金配合物与槟榔二鎓盐可进行有效的交叉偶联。黄金（I）-黄金（III）的氧化还原循环可以在两种不同的条件下进行，即可见光光氧化还原以及热诱导的自由基链途径。目前在金中具有催化作用的C（sp 2）C（sp 2）交叉偶联方案将为传统的交叉偶联化学提供所需的结构多样性。
• Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins
  作者：Yili Shi、Katrina E. Roth、Stephen D. Ramgren、Suzanne A. Blum

  DOI：10.1021/ja9068497

  日期：2009.12.23

  A new strategy for gold and palladium dual-catalytic reactivity and turnover, called catalyzed catalysis, enhanced the synthetic usefulness of vinylgold intermediates by providing dual-catalytic carbon-carbon cross-coupling as an alternative to protodemetalation. This protocol enabled the synthesis of substituted butenolides and isocoumarins from ally[ esters. Kinetic and spectroscopic experiments support a mechanism in which the Lewis acidic gold complex catalyzes both an initial rearrangement step and a subsequent Lewis basic palladium oxidative-addition step.