(3-fluorobenzyl)(p-tolyl)sulfane | 712296-58-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3-fluorobenzyl)(p-tolyl)sulfane
• 英文别名: 1-Fluoro-3-[(4-methylphenyl)sulfanylmethyl]benzene
• CAS: 712296-58-7
• 化学式: C₁₄H₁₃FS
• 分子量: 232.322
• InChiKey: WBZIASFKRYIKMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-fluorobenzyl)(p-tolyl)sulfane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-fluoro-3-((p-tolylsulfinyl)methyl)benzene
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j
• 作为产物：
  描述：

  4-甲苯硫酚 在 锰 、 4,4'-二甲基-2,2'-联吡啶 、 copper(l) chloride 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 (3-fluorobenzyl)(p-tolyl)sulfane
  参考文献：
  名称：

  铜催化 N-二硫代邻苯二甲酰亚胺和卤代烷的化学选择性偶联：不对称二硫化物和硫化物的合成

  摘要：

  在本文中，我们报道了前所未有的铜催化二硫化物或硫化物偶联反应，涉及未活化的烷基卤化物和N-二硫代邻苯二甲酰亚胺。该反应可以在温和的条件下使用低成本的金属催化剂进行，并表现出较高的化学选择性和官能团兼容性，能够有效组装各种硫化物和二硫化物。

  DOI：

  10.1021/acs.orglett.4c01109

文献信息

• Palladium-Catalyzed C–H Alkenylation of Arenes Using Thioethers as Directing Groups
  作者：Ming Yu、Yongju Xie、Chunsong Xie、Yuhong Zhang

  DOI：10.1021/ol3006997

  日期：2012.4.20

  Thioethers have been proven to be reliable directing groups for palladium catalyzed alkenylation of arenes via C–H activation. Mechanistic investigation reveals that the C–H cleavage of arenes is the turnover-limiting step, and an acetate-bridged dinuclear cyclopalladation intermediate is involved. The alkenylated thioethers can be easily removed and transformed into a variety of useful groups.

  硫醚已被证明是通过C–H活化进行钯催化的芳烃链烯基化反应的可靠导向基团。机理研究表明，芳烃的C–H裂解是限制周转的步骤，并且涉及到乙酸酯桥联的双核环palpalladation中间体。烯基化的硫醚可以容易地除去并转化成各种有用的基团。
• Interception of benzyne with thioethers: a facile access to sulfur ylides under mild conditions
  作者：Hua-Dong Xu、Mao-Qiang Cai、Wei-Jie He、Wen-Hao Hu、Mei-Hua Shen

  DOI：10.1039/c3ra47206j

  日期：——

  has been trapped in situ by thioethers to give sulfonium ylides, which in turn have been intercepted by isatins to give rise to corresponding spiroepoxy oxindoles in moderate to high yields. This reaction provides a facile and efficient synthesis of spiroepoxy oxindoles.

  在CsF作用下，由三氟甲磺酸邻-（三甲基甲硅烷基）苯基生成的反应性苯炔已被硫醚原位捕获，生成了化，然后被靛红截获，从而以中等至高收率生成了相应的螺环氧丙烷。该反应提供了螺环氧基羟吲哚的简便而有效的合成。
• Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization
  作者：Binjie Wang、Yue Liu、Cong Lin、Yiming Xu、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/ol502127j

  日期：2014.9.5

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.
• Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups
  作者：Binjie Wang、Chuang Shen、Jinzhong Yao、Hong Yin、Yuhong Zhang

  DOI：10.1021/ol402921w

  日期：2014.1.3

  A novel palladium-catalyzed ortho-C(sp(2))-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.
• Copper-Catalyzed Chemoselective Coupling of <i>N</i>-Dithiophthalimides and Alkyl Halides: Synthesis of Unsymmetrical Disulfides and Sulfides
  作者：Bin Li、Bo-Xi Liu、Weidong Rao、Shu-Su Shen、Daopeng Sheng、Shun-Yi Wang

  DOI：10.1021/acs.orglett.4c01109

  日期：——

  In this paper, we report an unprecedented copper-catalyzed disulfides or sulfides coupling reaction involving unactivated alkyl halides and N-dithiophthalimides. This reaction can be conducted under mild conditions using low-cost metal catalysts and exhibits high chemical selectivity and functional group compatibility, enabling the efficient assembly of various sulfides and disulfides.

  在本文中，我们报道了前所未有的铜催化二硫化物或硫化物偶联反应，涉及未活化的烷基卤化物和N-二硫代邻苯二甲酰亚胺。该反应可以在温和的条件下使用低成本的金属催化剂进行，并表现出较高的化学选择性和官能团兼容性，能够有效组装各种硫化物和二硫化物。