1-(1-chloro-2-phenylethyl)-4-(trifluoromethyl)benzene | 1228032-96-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(1-chloro-2-phenylethyl)-4-(trifluoromethyl)benzene
• CAS: 1228032-96-9
• 化学式: C₁₅H₁₂ClF₃
• mdl: MFCD19155583
• 分子量: 284.708
• InChiKey: BUAPVWYWMSZODT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对三氟甲基苯乙烯 、 三丁基苯基锡 在 二(氰基苯)二氯化钯 、 (二氯碘)-苯 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以78%的产率得到1-(1-chloro-2-phenylethyl)-4-(trifluoromethyl)benzene
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Arylhalogenation of Alkenes: Synthetic Scope and Mechanistic Insights

  摘要：

  This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse alpha-olefins by oxidatively intercepting Mizoroki-Heck intermediates. These transformations afford synthetically useful 1,2- and 1,1-arylhalogenated products in good yields with good to excellent selectivities that can be modulated by changing the nature of the halogenating reagent and/or the reaction conditions. The selectivity of these reactions can be rationally tuned by (i) controlling the relative rates of oxidative functionalization versus beta-hydride elimination from equilibrating Pd-II-alkyl species and (ii) stabilization of organometallic Pd-II intermediates through the formation of pi-benzyl adducts. These arylhalogenations exhibit modest to excellent levels of stereoselectivity, and the key carbon-halogen bond-forming step proceeds with predominant retention of stereochemistry at carbon.

  DOI：

  10.1021/ja101851v

文献信息

• A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes
  作者：Bo Li、Ala Bunescu、Daniel Drazen、Katherine Rolph、Jean Michalland、Matthew J. Gaunt

  DOI：10.1002/anie.202405939

  日期：2024.8.19

  Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.