4-(2-phenylallyl)-1,1'-biphenyl | 1190259-74-5

• 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: 4-(2-phenylallyl)-1,1'-biphenyl
• 英文别名: 4-(2-phenylallyl)-1,1′-biphenyl
• CAS: 1190259-74-5
• 化学式: C₂₁H₁₈
• 分子量: 270.374
• InChiKey: TZZNCLAOGHNZRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  alpha- 溴苯乙烯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 、 silver carbonate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 4-(2-phenylallyl)-1,1'-biphenyl
  参考文献：
  名称：

  钯催化的银促进取代的烯丙基三甲基硅烷与芳基碘的交叉偶联

  摘要：

  开发了无配位体的钯催化的取代的烯丙基（三甲基）硅烷与由银盐形成的芳基碘化物的交叉偶联。该反应通过化学选择性和区域选择性递送烯丙基芳烃。研究表明该反应可能通过将ArI氧化加成到Pd（0）上，然后进行卤化物的抽提而得到亲电配合物ArPdX，后者通过亲电加成/去甲硅烷基化/还原消除反应与烯丙基三甲基硅烷进一步反应得到烯丙基芳基偶联剂产品。

  DOI：

  10.1016/j.tetlet.2018.11.026

文献信息

• Sulfur-Mediated Allylic C–H Arylation, Epoxidation, and Aziridination
  作者：Hang Luo、Gang Hu、Pingfan Li

  DOI：10.1021/acs.joc.9b01438

  日期：2019.9.6

  arylation, epoxidation, and aziridination were realized through one-pot procedures. The reaction design involved initial addition between olefins and triflic anhydride activated sulfoxides, followed by subsequent reactions of the allylic sulfur ylides generated under basic conditions with arylboronic acids, aldehydes, or aldimines, to give allylic arylation, epoxidation, or aziridination products, respectively

  通过一锅法实现了无过渡金属，硫介导的烯丙基CH芳基化，环氧化和叠氮化。反应设计包括先在烯烃和三氟甲磺酸酐活化的亚砜之间添加，然后在碱性条件下生成的烯丙基硫烷基化物与芳基硼酸，醛或醛亚胺进行后续反应，分别得到烯丙基芳基化，环氧化或叠氮化产物。
• Oxidative cross-coupling of allyl(trimethyl)silanes with aryl boronic acids by palladium catalysis
  作者：Zhibing Zhou、Zhen-Lin Hou、Fan Yang、Bo Yao

  DOI：10.1016/j.tet.2018.10.055

  日期：2018.12

  allylsilanes with aryl boronic acids has been developed by palladium catalysis. The reaction between β-substituted allyl(trimethyl)silanes and a wide range of aryl boronic acids afforded allylarenes in moderate to good yields and excellent selectivity. On the basis of experimental results and literature reports, it was suggested that the reaction might start from transmetalation of aryl boronic acid with AgOAc

  烯丙基硅烷与芳基硼酸的第一次氧化交叉偶联已通过钯催化发展。β-取代的烯丙基（三甲基）硅烷与各种芳基硼酸之间的反应以中等至良好的产率和优异的选择性提供了烯丙基芳烃。根据实验结果和文献报道，有人认为该反应可能始于芳基硼酸与AgOAc的重金属化反应，然后与Pd（II）的重金属化反应，从而制得乙酸芳基钯配合物作为关键中间体。将该中间体与烯丙基硅烷进行亲电加成/去甲硅烷基化或金属转移，然后还原消除，得到最终产物。
• Photoredox‐ and Nickel‐Catalyzed Hydroalkylation of Alkynes with 4‐Alkyl‐1,4‐dihydropyridines: Ligand‐Controlled Regioselectivity
  作者：Yulin Zhang、Yoshiaki Tanabe、Shogo Kuriyama、Yoshiaki Nishibayashi

  DOI：10.1002/chem.202200727

  日期：2022.6.27

  Dual photoredox- and nickel-catalyzed hydroalkylation of terminal alkynes with 4-alkyl-1,4-dihydropyridines under visible light irradiation to afford Markovnikov or anti-Markovnikov-type alkylated alkenes in good-to-high yields has been achieved, in which the regioselectivity of the products was effectively controlled by coordination ligands for nickel catalysts. With [Ir(Fppy)3] (Fppy=3,5-difluor

  在可见光照射下，末端炔烃与 4-烷基-1,4-二氢吡啶的双重光氧化还原和镍催化加氢烷基化，以良好至高的产率获得了马尔科夫尼科夫或反马尔科夫尼科夫型烷基化烯烃，其中镍催化剂的配位体有效地控制了产物的区域选择性。以 [Ir(Fppy) 3 ] (Fppy=3,5-difluoro-2-(2-pyridyl)phenyl) 作为光氧化还原催化剂，使用 [NiCl 2 (dtbbpy)] (dtbbpy=4,4'-di- tert -丁基-2,2'-联吡啶）或NiCl 2  ⋅ 6 H 2 O作为镍催化剂分别导致马尔科夫尼科夫型或反马尔科夫尼科夫型产物的选择性形成。
• Selective arylation of 1,1-disubstituted olefins using a biphenyl-based phosphine in Heck coupling reactions
  作者：Shirin Nadri、Mohammad Joshaghani、Ezzat Rafiee

  DOI：10.1016/j.tetlet.2009.07.052

  日期：2009.9

  The biphenyl-based phosphine, 2-diphenylphosphino-2'-methylbiphenyl is an effective ligand for palladium-catalyzed terminal arylation of 1,1-disubstituted olefins with aryl bromides in DMF and K2CO3 as base. The yields of products are independent of the electronic properties of the aryl bromides, however, the nature of the olefin has a major effect. (C) 2009 Elsevier Ltd. All rights reserved.