tri(p-tolyl)antimony diacetate | 73694-89-0

• 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: tri(p-tolyl)antimony diacetate
• 英文别名: tris(p-tolyl)antimony diacetate；Tri-p-tolylantimony diacetate；[acetyloxy-tris(4-methylphenyl)-λ5-stibanyl] acetate
• CAS: 73694-89-0
• 化学式: C₂₅H₂₇O₄Sb
• 分子量: 513.237
• InChiKey: JIFLSIWFCCFZCQ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 tri(p-tolyl)antimony diacetate 在 bis-triphenylphosphine-palladium(II) chloride 、 氧气 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以99%的产率得到1-甲基-4-苯基乙炔苯
  参考文献：
  名称：

  Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition

  摘要：

  A simple copper- and base-free palladium-catalyzed Sonogashira-type cross-coupling by the use of triarylantimony dicarboxylates is described. Reaction of triarylantimony diacetates with terminal alkynes in the presence of 1 mol% of PdCl2(PPh3)(2) Catalyst led to the formation of cross-coupling products in good to excellent yields. The reaction proceeded effectively under an aerobic condition, in that two of the three aryl groups on antimony could be transferred to the coupling products, whereas only one of them was involved in the reaction in an argon atmosphere. The reaction is sensitive to the electronic nature of the diacetates, and those bearing an electron-withdrawing group on the aromatic ring showed higher reactivity than those having an electron-donating group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.113
• 作为产物：
  描述：

  三(对甲苯基)锑 、 3,5-diacetoxyiodobenzene 以 二氯甲烷 为溶剂， 生成 tri(p-tolyl)antimony diacetate
  参考文献：
  名称：

  Pd(0)–Cu(I)-catalyzed cross-coupling of alkynylsilanes with triarylantimony(V) diacetates

  摘要：

  在50°C下，以CH3CN为溶剂，使用5 mol%的Pd2(dba)3·CHCl3和10 mol%的CuI处理炔基硅烷与三芳基锑二醋酸酯，反应5小时，获得了良好的芳基取代炔烃产率。另一方面，也可以在常压下直接进行三芳基锑二醋酸酯与炔基硅烷的羰基偶联反应。

  DOI：

  10.1039/b007800j

文献信息

• Suzuki-type cross-coupling reaction of pentavalent triarylantimony diacetates with arylboronic acids without a base
  作者：Shuji Yasuike、Weiwei Qin、Yoshiyuki Sugawara、Jyoji Kurita

  DOI：10.1016/j.tetlet.2006.10.163

  日期：2007.1

  Novel base-free Suzuki-type cross-coupling reaction by the use of triarylantimony diacetates and arylboronic acids in the presence of Pd(PPh3)4 catalyst led to the formation of biaryl derivatives in moderate to excellent yields. The reaction is applicable to a variety of arylboronic acids bearing base-sensitive functional groups.

  在Pd（PPh 3）4催化剂存在下使用三芳基锑酸二乙酸酯和芳基硼酸的新型无碱Suzuki型交叉偶联反应导致联芳基衍生物的形成具有中等至极好的收率。该反应适用于各种带有碱敏感官能团的芳基硼酸。
• Triarylantimony dicarboxylates as pseudo-halides for palladium-catalyzed cross-coupling reaction with arylboronic acids and triarylbismuthanes without any base
  作者：Weiwei Qin、Shuji Yasuike、Naoki Kakusawa、Yoshiyuki Sugawara、Masatoshi Kawahata、Kentaro Yamaguchi、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2007.10.030

  日期：2008.1

  diacetates (6) with organoboron reagents (9) in the presence of Pd(PPh3)4 led to the formation of cross-coupling products, biaryls (10, 12 and 14–17), in moderate to excellent yields under mild conditions without any base. Similar reaction of 6 with triarylbismuthanes (18) also gave the corresponding cross-coupling products. Single crystal X-ray analysis of tri(p-tolyl)antimony diacetate (6b) and tris(p-

  所述triarylantimony二乙酸酯的（反应6）与有机硼试剂（9中的Pd（PPh的存在下）3）4导致交叉耦合产物的形成，联芳基化合物（10，12和14 - 17，在中度至良好的产率）在没有任何碱的温和条件下。6与三芳基双muthanes（18）的相似反应也得到相应的交叉偶联产物。三（对甲苯基）二乙酸锑（6b）和三（对三氟甲基苯基）二乙酸锑（6e）的单晶X射线分析）揭示了两个中心锑原子的几何形状都介于三角形双锥体和五边形双锥体排列之间，并且锑和两个具有顺式取向的羰基氧原子之间存在分子内配位。
• Pd-catalyzed C-arylation of unsaturated compounds with pentavalent triarylantimony dicarboxylates
  作者：Dmitry V Moiseev、Aleksey V Gushchin、Andrey S Shavirin、Yury A Kursky、Viktor A Dodonov

  DOI：10.1016/s0022-328x(02)02179-4

  日期：2003.2

  Triarylantimony(V) derivatives Ar3SbX2 (X=Hal or acyloxy) were prepared by reaction of Ar3Sb with equimolar amounts of a peroxide ROOH (R=t-Bu, H) in the presence of an acid or an anhydride in good to excellent yields. Ar3Sb(O2CR)2 are mild and efficient C-arylation reagents of unsaturated compounds (methyl acrylate, styrene, 2-phenylpropene and acrylonitrile) under palladium catalysis at 50 °C, with

  三芳基锑（V）衍生物Ar 3 SbX 2（X = Hal或酰氧基）是通过Ar 3 Sb与等摩尔量的过氧化物ROOH（R ​​= t- Bu，H）在酸或酸酐的存在下反应制得的。好到极好的产量。Ar 3 Sb（O 2 CR）2是钯在50°C的催化下，不饱和化合物（丙烯酸甲酯，苯乙烯，2-苯基丙烯和丙烯腈）的温和有效的C-芳基化试剂，PdCl 2是最有效的催化剂。Ar 3 SbHal 2在这些条件下不反应。
• Pd-Catalyzed P-Arylation of Triarylantimony Dicarboxylates with Dialkyl H-Phosphites without a Base: Synthesis of Arylphosphonates
  作者：Mio Matsumura、Yuqiang Dong、Naoki Kakusawa、Shuji Yasuike

  DOI：10.1248/cpb.c14-00727

  日期：——

  The reaction of triarylantimony diacetates [Ar3Sb(OAc)2] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh3)4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon–phosphorus bond formation by using an organoantimony compound as a pseudo-halide.

  三芳基锑二乙酸酯[Ar3Sb(OAc)2]与二烷基次膦酸酯[H-PO(OR)2]在Pd(PPh3)4（5摩尔%）催化剂存在下进行反应，无需添加碱即可中等至极好产率地生成芳基膦酸酯。这种反应是首次利用有机锑化合物作为假卤化物的碳磷键形成实例。
• Palladium-catalyzed regioselective arylation of silyloxy compounds with triarylantimony diacetates
  作者：Suk-Ku Kang、Hyung-Chul Ryu、Young-Taek Hong

  DOI：10.1039/b006431i

  日期：——

  The palladium-catalyzed arylation of enol silyl ethers, siloxydienes, silyloxycyclopropane with triarylantimony diacetates was carried out in the presence of PdCl2(CH3CN)2 (5 mol%) in DME–CH3CN at room temperature under mild conditions.

  在温和条件下，使用PdCl2(CH3CN)2 (5 mol%) 在DME–CH3CN中的室温下，进行钯催化的烯醇硅醚、硅氧烯烃、硅氧基环丙烷与三芳基锑二乙酸盐的芳基化反应。