甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) | 1445085-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II)
• 中文别名: 甲烷磺酸(2-二环己基膦基-2',4',6'-三异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II)
• 英文名称: XPhos Pd G3
• 英文别名: (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate；Pd-XPhos G3；xphosG3；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate；methanesulfonato(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)；methanesulfonato(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)；tBuXPhos-Pd-G3；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) methanesulfonate；xphos palladacycle Gen 3；XantPhos Pd G3；XPhos Pd G4；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(ll) methanesulfonate；methanesulfonato(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium；[2-(2-aminophenyl)phenyl]palladium(dicyclohexyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphane)methanesulfonate；XPhos-G3-Palladacycle；RuPhos Pd G3；methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II)；[(2-dicyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1'-biphenyl)-2-(2’-amino-1,1’-biphenyl)]palladium(II)methanesulfonate；methanesulfonato (2-dicyclohexylphosphino-2’,4’,6’-tri-isopropyl-1,1’-biphenyl)(2’-amino-1,1’-biphenyl-2-yl)palladium (II)；(2-dicyclohexylphosphino-2‘,4‘,6‘-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2‘,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2‘,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(ll) methanesulfonate；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’- biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II)methanesulfonate；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(ll) methanesulfonate；methanesulfonato(2-dicyclohexylphosphino-2’,4’,6’-tri-i-propyl-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II)；methanesulfonato(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’- biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II)；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1'- biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(lI) methanesulfonate；methanesulfonato (2-dicyclohexylphosphino-2’,4’,6’-tri-i-propyl-1,1‘-biphenyl)(2’-amino-1,1-biphenyl-2-yl)palladium(ll)；methanesulfonato-(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1’-bipheny)(2’-amino-1,1’-biphenyl-2-yl)palladium(ll)；(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate；methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)；methanesulfonic acid (2-dicyclohexylphosphino-2',4',6'-tri-isopropyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium (II)；(2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate；(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(lI) methanesulfonate；chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II)；3rd generation x-phos palladacycle；3rd generation XPhos precatalyst；XPhos‐Pd‐G3；X-phos G₃Pd；X-phosPd 3G；XPhos Pd G2；XPhos Palladacycle Gen. 3；dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonate;palladium(2+);2-phenylaniline
• CAS: 1445085-72-2
• 化学式: C₄₆H₆₂NO₃PPdS
• 分子量: 846.463
• InChiKey: LMRGIWYBLKXQGS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  12.39
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (碘甲基)三氟硼酸钾 、 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Mechanism-Based Design and Optimization of a Catalytic Electrophilic Cyclopropanation without Diazomethane

  摘要：

  Iodomethylboron compounds, either the trifluoroborate or a boronic ester, cyclopropanate electron-rich olefins and unprotected allylic alcohols with Pd catalysts according to a novel, designed catalytic cycle. Proposed intermediates in a "diverted Heck" mechanism are observed by means of spectroscopic studies and by isolation and X-ray crystallographic characterization, which together with reaction kinetics point to a separation of rate-determining and product-determining steps, and a mechanism-based optimization of the yield, selectivity, and scope of the catalytic electrophilic cyclopropanation. The reaction with crystalline, air-stable, nonhygroscopic, and nontoxic reagents provides an alternative to Simmons Smith-type reactions, as well as cyclopropanation procedures that require the use of diazomethane.

  DOI：

  10.1021/acs.organomet.6b00531
• 作为产物：
  描述：

  2-ammoniumbiphenyl mesylate 以 四氢呋喃 、 甲苯 为溶剂， 生成 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II)
  参考文献：
  名称：

  用于 C–C 和 C–N 交叉偶联反应的新型钯预催化剂的设计和制备†

  摘要：

  已经制备了一系列基于 2-氨基联苯支架的易于制备的膦连接钯预催化剂。已经研究了前催化剂相关的不稳定卤化物（或拟卤化物）在钯环的形成和稳定性中的作用。发现用甲磺酸盐代替先前版本的预催化剂中的氯化物产生了一类具有改进的溶液稳定性并且易于从更广泛的膦配体制备的新类型的预催化剂。探讨了先前版本的 precatalyst 与此处报告的版本之间的差异。此外，后者的反应性在一系列 C-C 和 C-N 键形成反应中进行了检查。

  DOI：

  10.1039/c2sc20903a
• 作为试剂：
  描述：

  2-chloro-6-(trifluoromethyl)pyridin-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 氯化亚砜 、 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  WO2024094170A1

  摘要：

  公开号：

文献信息

• Phosphine-Ligated Palladium Sulfonate Palladacycles
  申请人：Massachusetts Institute of Technology

  公开号：US20130331566A1

  公开（公告）日：2013-12-12

  Described are palladium precatalysts, and methods of making and using them. The palladium precatalysts show improved stability and improved reactivity in comparison to previously-described palladium precatalysts.

  描述了钯前催化剂及其制备和使用方法。与先前描述的钯前催化剂相比，这些钯前催化剂表现出更高的稳定性和更高的反应性。
• Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions
  作者：Nicholas C. Bruno、Matthew T. Tudge、Stephen L. Buchwald

  DOI：10.1039/c2sc20903a

  日期：——

  of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with

  已经制备了一系列基于 2-氨基联苯支架的易于制备的膦连接钯预催化剂。已经研究了前催化剂相关的不稳定卤化物（或拟卤化物）在钯环的形成和稳定性中的作用。发现用甲磺酸盐代替先前版本的预催化剂中的氯化物产生了一类具有改进的溶液稳定性并且易于从更广泛的膦配体制备的新类型的预催化剂。探讨了先前版本的 precatalyst 与此处报告的版本之间的差异。此外，后者的反应性在一系列 C-C 和 C-N 键形成反应中进行了检查。
• Mechanism-Based Design and Optimization of a Catalytic Electrophilic Cyclopropanation without Diazomethane
  作者：Augustin A. S. W. Tchawou、Mihai Raducan、Peter Chen

  DOI：10.1021/acs.organomet.6b00531

  日期：2017.1.9

  Iodomethylboron compounds, either the trifluoroborate or a boronic ester, cyclopropanate electron-rich olefins and unprotected allylic alcohols with Pd catalysts according to a novel, designed catalytic cycle. Proposed intermediates in a "diverted Heck" mechanism are observed by means of spectroscopic studies and by isolation and X-ray crystallographic characterization, which together with reaction kinetics point to a separation of rate-determining and product-determining steps, and a mechanism-based optimization of the yield, selectivity, and scope of the catalytic electrophilic cyclopropanation. The reaction with crystalline, air-stable, nonhygroscopic, and nontoxic reagents provides an alternative to Simmons Smith-type reactions, as well as cyclopropanation procedures that require the use of diazomethane.