(2,4-dimethylphenyl)(4-methoxyphenyl)sulfane | 1420042-86-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2,4-dimethylphenyl)(4-methoxyphenyl)sulfane
• 英文别名: 1-(4-Methoxyphenyl)sulfanyl-2,4-dimethylbenzene
• CAS: 1420042-86-9
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: MUZQOQNPZUIDSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘苯甲醚 、 2,4-二甲基苯硫酚 在 吡啶 、 2,2'-联吡啶 、 nickel dichloride 、 锌 作用下， 以 甲醇 为溶剂， 以55%的产率得到(2,4-dimethylphenyl)(4-methoxyphenyl)sulfane
  参考文献：
  名称：

  Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

  摘要：

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.

  DOI：

  10.1021/ol303366u

文献信息

• Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B ₂ pin ₂
  作者：Rongkang Wang、Fangming Chen、Lvqi Jiang、Wenbin Yi

  DOI：10.1002/adsc.202001518

  日期：2021.3.29

  arylazo sulfones were used as radical precursors for carbon‐heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and

  已经开发了一种有效的各种不对称硫醚和芳基硼酸酯的电化学合成方法。台式稳定的芳基偶氮砜被用作在电化学条件下形成碳-杂原子键的自由基前体。此外，该方法的可扩展性是通过以克为单位对芳基偶氮砜与硫醇和B 2 pin 2进行电化学巯基化和硼化来评估的。该方案不仅避免了使用化学计量的氧化剂，金属催化剂，活化剂，甚至添加了碱，而且还表现出良好的官能团耐受性。
• Direct C–H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis
  作者：Ge Liang、Jing-Hao Wang、Tao Lei、Yuan-Yuan Cheng、Chao Zhou、Ya-Jing Chen、Chen Ye、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.1c03090

  日期：2021.10.15

  An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide radical cation plays a crucial role in the visible-light catalysis of aerobic thiolation. Simply controlling the equivalent ratio of substrates enables

  报道了一种无氧金属、可见光诱导的苯酚与苯硫酚的区域选择性硫醇化反应。交叉偶联方案表现出良好的官能团耐受性和高区域选择性。机理研究表明，二硫化物自由基阳离子在有氧硫醇化的可见光催化中起着至关重要的作用。简单地控制底物的当量比，可以在一锅反应中选择性地形成具有高活性的硫化物或亚砜产物。
• Coupling of thiols and aromatic halides promoted by diboron derived super electron donors
  作者：Mario Franco、Emily L. Vargas、Mariola Tortosa、M. Belén Cid

  DOI：10.1039/d1cc05294b

  日期：——

  We have proven that pyridine–boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized

  我们已经证明，吡啶-硼基复合物可用作超电子供体，通过 S RN 1 机制促进硫醇和芳族卤化物的偶联。该反应适用于广泛的底物范围，可耐受杂环，包括吡啶、可烯醇化或可还原的官能团。该方法已通过受控和连续的分子内电子转移过程应用于药物合成中的中间体以及有趣的功能化聚硫醚。
• Iodine(III) Enabled Dehydrogenative Aryl C−S Coupling by in situ Generated Sulfenium Ion
  作者：Khokan Choudhuri、Saikat Maiti、Prasenjit Mal

  DOI：10.1002/adsc.201801510

  日期：2019.3.5

  Due to the normal polarity preferences, arenes form stable complexes with thiols through S−H⋅⋅⋅π interaction and direct dehydrogenative aryl C−S coupling is usually restricted. We report here an umpolung based one pot and direct C−S coupling approach under metal free and mild condition. Electrophile sulfenium ions were generated in situ from thiols using iodine(III) reagent PhI(OAc)2 (PIDA) and subsequently

  由于正常的极性偏好，芳烃通过SH·⋅·π相互作用与硫醇形成稳定的络合物，通常直接脱氢芳基CS偶联受到限制。我们在这里报告了一种在无金属和温和条件下基于umpolung的单罐和直接CS耦合方法。使用碘（III）试剂PhI（OAc）2（PIDA）从硫醇中原位生成亲电子sulf离子，然后将其用于芳族亲电子取代（EArS）以合成二芳基硫醚。同样通过使用适量的PIDA，CS和S = O键的级联合成可在一锅中产生芳基亚硫酰基芳烃。共价自选或竞争实验进一步证实了sulf离子参与了EArS。
• Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst
  作者：Paul H. Gehrtz、Valentin Geiger、Tanno Schmidt、Laura Sršan、Ivana Fleischer

  DOI：10.1021/acs.orglett.8b03476

  日期：2019.1.4

  aryl chlorides and in situ generated aliphatic and aromatic thiolates is described. The employed on-cycle, air-stable defined Ni precatalysts allow for transformation of a broad scope of substrates. A variety of functional groups and heterocyclic motifs as well as structurally varied thiols are tolerated at unprecedented moderate catalyst loadings and reaction temperatures. Depending on reaction conditions

  描述了具有挑战性的芳基氯化物和原位生成的脂族和芳族硫醇盐的一般和高效的镍催化偶联。所使用的循环中，空气稳定的Ni定义型预催化剂可实现广泛范围的底物转化。在前所未有的中等催化剂负载量和反应温度下，可以耐受各种官能团和杂环基序以及结构上不同的硫醇。根据反应条件，芳基硫醇可以选择性地进行CS或CC偶联。