tris(o-tolyl)antimony diacetate | 209287-67-2

• 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: tris(o-tolyl)antimony diacetate
• CAS: 209287-67-2；23845-57-0
• 化学式: C₂₅H₂₇O₄Sb
• 分子量: 513.237
• InChiKey: RLZKHYXOTITBRQ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 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：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 tris(o-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68%的产率得到1-甲基-2-(苯基乙炔基)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：

  2-碘代甲苯 生成 tris(o-tolyl)antimony diacetate
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sb: Org.Comp.1, 1.1.1.1.8, page 96 - 106

  摘要：

  DOI：

文献信息

• 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。
• Synthesis, Structure, and Reactions of (Acylimino)triaryl-λ⁵-bismuthanes:  First Comparative Study of the (Acylimino)pnictorane Series
  作者：Yoshihiro Matano、Hazumi Nomura、Hitomi Suzuki、Motoo Shiro、Haruyuki Nakano

  DOI：10.1021/ja003623l

  日期：2001.11.1

  The synthesis, structure, and reactions of (acylimino)triaryl-lambda(5)-bismuthanes and a comparative study of the structure and reactivity of a series of (acylimino)pnictoranes are reported. Treatment of ortho-substituted triarylbismuth dichlorides 1 (Ar(3)BiCl(2); Ar = 2-MeC(6)H(4), 2-MeOC(6)H(4), 2,4,6-Me(3)C(6)H(2)) with amides 2 (H(2)NCOR; R = CF(3), CCl(3), 3,5-(CF(3))(2)C(6)H(3)) in the presence

  报道了（酰基亚氨基）三芳基-λ(5)-铋烷的合成、结构和反应，以及一系列（酰基亚氨基）pnictoranes 的结构和反应性的比较研究。邻位取代三芳基铋二氯化物的处理 1 (Ar(3)BiCl(2); Ar = 2-MeC(6)H(4), 2-MeOC(6)H(4), 2,4,6-Me( 3)C(6)H(2)) 与酰胺 2 (H(2)NCOR; R = CF(3), CCl(3), 3,5-(CF(3))(2)C(6) H(3)) 在二氯甲烷中 2.2 当量 KO-t-Bu 的存在下以 77-96% 的产率提供（酰基亚氨基）三芳基-λ（5）-铋烷 3（Ar(3)Bi=NCOR）。邻位取代芳基配体和吸电子 N 取代基分别为反应性 Bi=N 键提供动力学和热力学稳定性。一系列（酰基亚氨基）pnictoranes (Ar(3)M=NCOR and H(3)M=NCOCF(3); M = P, As
• Adducts of tertiary stibines with mercury(II) halides
  作者：G. Deganello、G. Dolcetti、M. Giustiniani、U. Belluco

  DOI：10.1039/j19690002138

  日期：——

  The preparation of Lewis-acid–base adducts of the type R3SbHgX2(R = phenyl, o- and p-tolyl; X = Cl, Br, and I) are reported. Reaction of the o-tolylstibine with HgCl2 in benzene yields Hg2Cl2 and R3SbCl2. In tetrahydrofuran the reaction products are R2SbCl and RHgCl. These results are interpreted in terms of a scrambling occurring via a five-co-ordinate antimony labile intermediate formed via oxidative

  据报道，制备了R 3 SbHgX 2类型的路易斯酸碱加合物（R =苯基，邻甲苯基和对甲苯基； X = Cl，Br和I）。所述的反应ö与升汞-tolylstibine 2在苯产生汞柱2氯2和R 3的SbCl 2。在四氢呋喃中，反应产物为R 2 SbCl和RHgCl。这些结果以通过五坐标锑不稳定中间体发生的加扰来解释，该中间体是通过HgCl 2氧化添加了锑而形成的。
• Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions
  作者：Shuji Yasuike、Yuqiang Dong、Naoki Kakusawa、Mio Matsumura、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2014.04.006

  日期：2014.8

  The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)(2) (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives. (C) 2014 Published by Elsevier B.V.