In(SPh)₃

• 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: In(SPh)₃
• 英文别名: indium(III) benzenethiolate；indium tri(benzenethiolate)；indium tri(phenylthiolate)；indium tris(phenylthiolate)；(PhS)3In
• 化学式: 3C₆H₅S*In
• 分子量: 442.335
• InChiKey: NZKNAFUZJNMLOC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  In(SPh)₃ 、 2,2'-联二噻吩 在 palladium diacetate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以90%的产率得到2-(phenylthio)-5-[5-(phenylthio)thiophen-2-yl]thiophene
  参考文献：
  名称：

  Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure

  摘要：

  Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-dibromopyridine reacted with indium tri(organothiolates) (0.68 equiv) in the presence of 4 mol A of Pd(OAc)(2), 4.2 mol % of Xantphos, and 1 equiv of diisopropylethylamine (DIPEA), producing disulfides in good to excellent yields. These results indicate that indium tri(organothiolates) transfer all three alkyl- or arylthio groups attached to indium metal to electrophilic coupling partners. Indium tri(organothiolates) derived from alkyl thiol having a low boiling point, such as n-propyl, isopropyl, and tert-butyl thiol, acted as good nucleophilic coupling partners. In addition, indium tri(arylthiolates) derived from aryl thiols possessing an electron-withdrawing or -donating group on the aromatic ring participated well in the Pd-catalyzed multifold carbon sulfur cross-coupling reaction. 4,4'-Dibromo-1,1'-biphenyl, 9,10-dibromoanthracene, 2,4-dibromoanisole, 2,7-dibromo-9,9-dimethylfluorene, 3,4-dibromothiophene, 2,3-dibromothiophene, 2,2'-bithiophene, 1,3,5-tribromobenzene, and 1,2,4,5-tetrabromobenzene were converted smoothly to the corresponding di-, tri-, and tetrasulfides.

  DOI：

  10.1021/jo102441t
• 作为产物：
  描述：

  indium 、 二苯二硫醚 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以89%的产率得到In(SPh)₃
  参考文献：
  名称：

  通过串联钯催化的取代和环异构化合成多取代的烯，呋喃和吡咯

  摘要：

  研究了炔丙基乙酸酯与有机硫醇铟的钯催化炔丙基取代反应，用于合成多取代的烯丙基硫化物。该程序可用于在一锅中通过串联钯催化的炔丙基取代和环异构化反应来合成多取代的呋喃和吡咯。

  DOI：

  10.1021/acs.orglett.6b03561
• 作为试剂：
  描述：

  N-fluoro-4-methyl-N-octylbenzenesulfonamide 在 copper acetylacetonate 、 indium 、 disodium hydrogenphosphate 、 1,10-菲罗啉 、 In(SPh)₃ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 9.0h， 以100%的产率得到4-甲基-N-辛基苯磺酰胺
  参考文献：
  名称：

  通过协同催化形成位点选择性Csp3-S键的一般方法

  摘要：

  在本文中，我们报道了铜催化的脂肪族胺Csp 3 -H键的位点选择性硫醇化。该方法具有广泛的底物范围和良好的官能团相容性。一级，二级和三级C–H键可以高效地转换为C–S键。还证明了通过这种方法对生物活性化合物的后期修饰。此外，实现了通过多米诺法一锅制备吡咯烷或哌啶化合物。

  DOI：

  10.1039/c9sc04169a

文献信息

• Synthesis of Substituted Coumarins via Brønsted Acid Mediated Condensation of Allenes with Substituted Phenols or Anisoles
  作者：Sundae Kim、Dongjin Kang、Chang-Hee Lee、Phil Ho Lee

  DOI：10.1021/jo301086k

  日期：2012.8.3

  Coumarins were obtained from the condensation of electron-rich arenes with allenes in the presence of TfOH in good yield. Depending on the substituent pattern of allenes employed, the general synthetic method of 4-substituted and 3,4-disubstituted 3-arylcoumarins has been developed. Readily available allenes were employed as the three-carbon atom sources constituting the coumarin skeleton.

  在TfOH存在下，富电子芳烃与丙二烯的缩合可得到香豆素。根据所用的烯的取代基样式，已经开发了4-取代和3，4-二取代的3-芳基香豆素的一般合成方法。使用现成的丙二烯作为构成香豆素骨架的三碳原子源。
• Palladium-Catalyzed Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolate) and Its Application to Sequential One-Pot Processes
  作者：Jae-Young Lee、Phil Ho Lee

  DOI：10.1021/jo801169h

  日期：2008.9.19

  tri(organothiolate) is an effective nucleophilic coupling partner in Pd-catalyzed C-S cross-coupling reactions to produce the functionalized sulfides in excellent yields with high atom efficiency and complete regio- and chemoselectivity. The present method was efficiently applied to the sequential one-pot processes composed of selective double C-S cross-coupling reactions and addition of allylindium or allenylindium

  发现三（有机硫代铟）铟是钯催化的CS交叉偶联反应中有效的亲核偶联配偶体，以高产率，高原子效率和完全的区域选择性和化学选择性产生官能化的硫化物。本方法有效地应用于由选择性双CS交叉偶联反应和将烯丙基或烯丙基铟加入醛缩醛以形成官能化的硫化物和双（硫化物）组成的顺序一锅法。
• Regioselective Markovnikov Hydrochalcogenation of Terminal Alkynes with Indium(III) Benzenechalcogenolates
  作者：Clovis Peppe、Liérson Borges de Castro、Melina de Azevedo Mello、Olga Soares do Rego Barros

  DOI：10.1055/s-2008-1072725

  日期：2008.5

  Indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) promote the rigorous Markovnikov hydrochalcogenation of terminal alkynes. The generality and limitations of the reaction with aminoalkynes leading to allylic amines bearing vinylic chalcogenide substituents are discussed.

  铟 (III) 苯硫属元素化物（硫属元素 = 硫和硒）促进末端炔烃的严格马尔科夫尼科夫加氢硫属元素化。讨论了与氨基炔烃反应生成带有乙烯基硫属化物取代基的烯丙胺的反应的一般性和局限性。
• Palladium-catalyzed Carbon–Sulfur Cross-coupling Reactions of Aryl Chlorides with Indium Tris(organothiolates)
  作者：Juntae Mo、Dahan Eom、Sung Hong Kim、Phil Ho Lee

  DOI：10.1246/cl.2011.980

  日期：2011.9.5

  Pd-Catalyzed carbon–sulfur cross-coupling reactions of aryl chlorides with indium tris(organothiolates) were developed. Aryl chlorides reacted with indium tris(organothiolates) (0.35 equiv) in the presence of 4 mol % of Pd(OAc)2, 4.2 mol % of Xantphos, and Cs2CO3 as an additive, producing aryl–aryl and aryl–alkyl sulfides in good to excellent yields.

  开发了钯催化的芳基氯化物与三(有机硫醇)铟的碳硫交叉偶联反应。在 4 摩尔%的 Pd(OAc)2、4.2 摩尔%的 Xantphos 和作为添加剂的 Cs2CO3 的存在下，芳基氯化物与三(有机硫醇)铟（0.35 等量）发生反应，生成芳基芳基和芳基烷基硫化物，产率从良好到极佳。
• In–E–MI ternary clusters (E = S, Se; MI= Cu, Ag): Synthesis, structural characterization and optical band gap energy evaluation
  作者：Melina de Azevedo Mello、Thaís Raquel Sossmeier、Bárbara Tirloni、Ernesto Schulz Lang

  DOI：10.1016/j.poly.2015.10.033

  日期：2015.12

  Abstract In this article we present the results of a study on the synthesis of In–E–MI ternary clusters (E = S, Se; MI = Cu, Ag) and an evaluation of the optical band gap energy. Characterization of three new compounds is reported: [Cu2In(PPh3)2SPh(μ-SPh)4] (1), [Cu2In(PPh3)2SePh(μ-SePh)4] (2) and [Ag2In(PPh3)2SPh(μ-SPh)4] (3). We discuss the hard-soft migratory tendency of the chalcogenolate ligands

  摘要在本文中，我们介绍了In-E-MI三元团簇（E = S，Se； MI = Cu，Ag）的合成研究以及对光带隙能量的评估的结果。报告了三种新化合物的表征：[Cu2In（PPh3）2SPh（μ-SPh）4]（1），[Cu2In（PPh3）2SePh（μ-SePh）4]（2）和[Ag2In（PPh3）2SPh（μ -SPh）4]（3）。我们讨论了硫属元素配体在所涉及的金属中心之间的软硬迁移趋势。另外，描述了用于获得纯结晶形式的所需产物的实验条件。这些方法可在短时间内提供良好的产量，并且可以获得用于有趣材料的单一来源的前体。