indium tris(isopropylthiolate)

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: indium tris(isopropylthiolate)
• 英文别名: indium tri(isopropylthiolate)；(i-PrS)3In；In(SPri)3
• 化学式: 3C₃H₇S*In
• 分子量: 340.284
• InChiKey: VVJADWTXEPFITF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  5.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2,5-二溴吡啶 、 indium tris(isopropylthiolate) 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91%的产率得到2,5-bis(isopropylthio)pyridine
  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：

  、 异丙硫醇 以 further solvent(s) 为溶剂， 以84%的产率得到indium tris(isopropylthiolate)
  参考文献：
  名称：

  Suh, Seigi; Hoffman, David M., Inorganic Chemistry, 1998, vol. 37, # 22, p. 5823 - 5826

  摘要：

  DOI：

文献信息

• 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。
• Synthesis of Multisubstituted Allenes, Furans, and Pyrroles via Tandem Palladium-Catalyzed Substitution and Cycloisomerization
  作者：Taekyu Ryu、Dahan Eom、Seohyun Shin、Jeong-Yu Son、Phil Ho Lee

  DOI：10.1021/acs.orglett.6b03561

  日期：2017.2.3

  A palladium-catalyzed propargyl substitution reaction of propargyl acetates with indium organothiolates is developed for the synthesis of multisubstituted allenyl sulfides. This procedure can be applied to the synthesis of multisubstituted furans and pyrroles via tandem palladium-catalyzed propargyl substitution and cycloisomerization reaction in one pot.

  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。
• 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。
• Synthesis of 2-Bromoimidazoles from Alkynes, <i>N</i>-Sulfonylazides, and Bromocyanides
  作者：Eunsook Lee、Taekyu Ryu、Eunji Shin、Jeong-Yu Son、Wonseok Choi、Phil Ho Lee

  DOI：10.1021/acs.orglett.5b00977

  日期：2015.5.15

  A synthetic method for Z-bromoimidazoles is developed from Rh-catalyzed cyclization of N-sulfonyl-1,2,3-triazoles with bromocyanides. Cu-catalyzed [3 + 2] cycloaddition followed by Rh-catalyzed cyclization starting from alkynes, N-sulfonylazides, and bromocyanides is also demonstrated for de novo synthesis of 2-bromoimidazoles in one pot. Moreover, this work was successfully employed to introduce diverse functional groups to the 2-position of imidazoles via cross-coupling reaction.
• [EN] METHODS FOR THE SYNTHESIS OF ORGANIC SULFIDES BY USING SULFIDES AND ORGANIC SULFUR-INDIUM COMPLEXES<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE SULFURES ORGANIQUES EN UTILISANT DES SULFURES ET DES COMPLEXES SOUFRE-INDIUM
  申请人：KNU INDUSTRY COOPERATION FOUND

  公开号：WO2009069888A3

  公开（公告）日：2010-07-15