lithium 3-methylthiophene-2-sulfinate | 1426432-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: lithium 3-methylthiophene-2-sulfinate
• 英文别名: Lithium;3-methylthiophene-2-sulfinate
• CAS: 1426432-85-0
• 化学式: C₅H₅O₂S₂*Li
• 分子量: 168.166
• InChiKey: WHJGTFBBUIREJW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.13
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸4-氰基苯基醚 、 lithium 3-methylthiophene-2-sulfinate 在 bis(acetylacetonato)palladium(II) 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到4-(3-methylthiophen-2-yl)benzonitrile
  参考文献：
  名称：

  Efficient Desulfinative Cross-Coupling of Heteroaromatic Sulfinates with Aryl Triflate in Environmentally Friendly Protic Solvents

  摘要：

  Aryl-substituted heteroaromatics were synthesized via desulfinative cross-coupling reactions using aryl triflate and heteroaromatic sulfinate coupling partners. This method uses synthetically versatile aryl triflates to access aryl-substituted heteroaromatics in good yields employing aqueous and alcoholic media without the use of base, additives or co-catalysts.

  DOI：

  10.3987/com-14-s(k)104
• 作为产物：
  描述：

  3-甲基噻吩 在 正丁基锂 、 二氧化硫 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 lithium 3-methylthiophene-2-sulfinate
  参考文献：
  名称：

  Efficient Desulfinative Cross-Coupling of Heteroaromatic Sulfinates with Aryl Triflate in Environmentally Friendly Protic Solvents

  摘要：

  Aryl-substituted heteroaromatics were synthesized via desulfinative cross-coupling reactions using aryl triflate and heteroaromatic sulfinate coupling partners. This method uses synthetically versatile aryl triflates to access aryl-substituted heteroaromatics in good yields employing aqueous and alcoholic media without the use of base, additives or co-catalysts.

  DOI：

  10.3987/com-14-s(k)104

文献信息

• Palladium-Catalyzed Intermolecular Desulfinylative Cross-Coupling of Heteroaromatic Sulfinates
  作者：Stéphane Sévigny、Pat Forgione

  DOI：10.1002/chem.201204201

  日期：2013.2.11

  in simplicity: An efficient and environmentally benign palladium‐catalyzed protocol has been developed using a sulfinate as a nucleophilic coupling partner. The sulfinate position is arylated chemoselectively in very good yields. The bench‐stable, non‐hygroscopic heteroaromatic sulfinate salts rapidly undergo cross‐coupling without the need of a co‐catalyst, base, or additives (see scheme; mw=microwave)

  美丽在于简单：使用亚磺酸盐作为亲核偶联伙伴，已经开发了一种高效且对环境无害的钯催化方案。亚磺酸酯位置以非常好的产率被化学选择性芳基化。稳定的，非吸湿性的杂芳族亚磺酸盐可以快速进行交叉偶联，而无需助催化剂，碱或添加剂（参见方案； mw =微波）。
• Efficient desulfinylative cross-coupling of thiophene and furan sulfinates with aryl bromides in aqueous media
  作者：Stéphane Sévigny、Pat Forgione

  DOI：10.1039/c3nj41153b

  日期：——

  This letter describes the development of an environmentally benign palladium-catalyzed cross-coupling reaction using heteroaromatic sulfinates as nucleophilic coupling partners in aqueous media. This method accesses aryl-substituted heteroaromatics in very good yields chemoselectively without the need for base, additives or co-catalysts.

  这封信描述了在水性介质中使用杂芳族亚磺酸盐作为亲核偶联伴侣的环境友好的钯催化交叉偶联反应的发展。该方法不需要碱，添加剂或助催化剂，就可以以化学选择性非常好的收率得到芳基取代的杂芳族化合物。